Pirates!
by Quest's Tails
Summary: What happens when Castiel, a discharged sailor from the navy, encounters the infamous pirate, Dean Winchester? Who knows what adventures, not to mention trouble, that these two could encounter on the high seas! This is based off of an AU I noticed on Tumblr, enjoy!
1. The Infamous Encounter

**Hello, this is based off of a post on Tumblr suggesting this AU, thought I'd give it a go!**

Castiel watched as the various sailors of various crews entered and exited throughout the large port of the seaside town, Darton. He sat on the beach, listening to the waves clash with the laughter of the sailors and the commanding voices of their superiors. Flashbacks of his adventures and his former mates began to gather in his mind, he shook his head to try and lose them

With a sigh Castiel sat up from his spot in the sand and headed towards the small pub on the edge of town.

It may be early, but he needed a drink.

* * *

His hat was tipped down, casting a shadow on Dean's face as he strode through the crowded street, everyone bustling and advertising their lovely merchandise. One woman, Dean didn't bother to look to hard at her after noticing the absent space where her fingers should have been, tried to pull him over, begging with a desperate look in her eyes.

Dean pulled away from the old hag, speeding up his pace as he tried to increase the distance from him and the strange woman. His coat danced a bit behind him, the dark brown cloth fluttering a bit as it caught on to the breeze his movement created. It wasn't until Dean reached the Town's Notice that he stopped, a certain face catching his eye on the large board.

"What a handsome devil," Dean smirked. He couldn't help but feel a puff of pride as he observed the wanted poster hanging on the board; his wanted poster. He grinned a little bit wider as he read the several charges he had collected from his career option.

"Well this calls for a celebration, after all they did such a good job on my face!" Dean rubbed his chin, trying to imitate the face they had drawn of him. Smiling he looked around, and walked over to one of the various vendors in the crowded street. He stopped in front of a large, stout man.

"Excuse me sir," Dean cleared his throat as he gave a charming smile to the man behind the stand. The man raised an eyebrow, Dean cleared his throat again before muttering "not one for chatter, I see."

"What do you need, kid?" The man spoke gruffly, waiting for Dean to answer him.

"Well, I was wondering if you could point me out to any good drinking establishments in this town?" Dean was mentally kicking himself in the head, _drinking establishments?_

The man stared at Dean for a second before answering the strange guy.

"There's a nice pub out on the edge of town by the port, small place but good service." Dean nodded and thanked the man before turning around and walking away from the vendor, a grin forming on his face among the shadows formed on his face.

* * *

Castiel sat in the dark pub, watching the few who were there mingling out of drunkenness while he sipped casually from his own drink. A rather large woman walked by him, casting her eyes across him. She winked at him, and Castiel quickly looked down and stared into his drink.

He waited until the lady had swaggered away that he looked back up, he had been focusing on trying to not let his cheeks burn too much while the woman had feasted her eyes on him.

Castiel quickly downed the rest of his drink of liquid courage before raising his glass to the bartender, who smiled. He walked over, bottle in hand to Castiel's table.

"How's the weather, sailor?" The bartender asked as he refilled the glass before taking the chair across from the dark-haired man. Castiel grimaced, and he took a sip of his drink before replying to the scrawny, blonde bartender.

"No longer a sailor, Alfie. I was discharged a couple months ago." Castiel stared into his drink, once again he began to remember the adventures, the ship and the crew. He quickly downed his drink and set the glass down a bit harshly.

Alfie smiled, his eyes sad and concerned as he poured the former sailor another drink.

"This one's on me Castiel. But you might want to take it easy, friend."

Castiel raised his glass as a sign of thanks, "It's okay Alfie," he took a sip and sighed as he put the glass down. "Okay, now I'm starting to feel something."

Laughing, the bartender pulled the glass across the table and downed the rest of Castiel's drink. He winked at the former sailor.

"I'm sure you'll figure out something to do, Castiel." Alfie knocked on the wood with his fist before standing up and heading back to the bar. Castiel sat in his chair and closed his eyes, the liquor in his system making him feel all fuzzy inside. But at the sound of the door opening, the former sailor opened his eyes to see who also found the need to have a drink while the sun still shone.

Eyes wide, Castiel's jaw almost dropped at the sight of who walked through that door.

* * *

Dean walked into the small bar, breathing in the various smells that wafted from its walls and people. He noticed that one man in a long, tan coat was staring at him. He raised an eyebrow at the strange man, who in turn looked down at his table. Dean began to feel odd vibes drifting from the guy, but he shook them off and headed towards the bartender.

"I'll have whatever's good," Dean told the bartender, smiling at the blond server. The bartender nodded, "Sure, pal. Go sit wherever and I'll- George! Leave the poor guy alone!" Dean smirked and nodded several times before turning around and choosing a table near the guy who had been eyeing him earlier.

Dean looked around the small pub, but his eyes kept getting drawn to the dark-haired man who sat a table across from him. The man kept his head down, although Dean noticed his eyes flicking around, most of the time towards the pirate himself. Dean was so distracted by the strange character that he jumped slightly when the bartender set his drink down in front of him.

He nodded and thanked the bartender who smiled, but was drawn away from Dean when he turned to settle the now growing quarrel between George and his target. Once again Dean smirked, but he found himself staring once more at the man. Deciding that he didn't like the growing pit in his stomach, Dean finished his drink and placed some of the coins on the table, calling out a thanks once more to the bartender before rushing out the door.

* * *

Castiel watched as the infamous Dean Winchester left the pub. After the cursed pirate stepped out Castiel stood up and followed, calling out a farewell to Alfie. The former sailor stood by the door, looking around for any sign of Dean.

Immediately his eyes lit up as he spotted the hat the Winchester had been wearing, so he ran. Castiel rushed through the street, pushing past the bustling crowds, his eyes trained on that one hat; that _one_ dark hat that bobbed up and down.

He was cutting the distance, but watched as the hat turned a corner. Castiel raced towards the alley and stopped as he reached the corner. He lay against the wall, his heart racing with excitement as he slowly looked around the corner.

It was then that a hand reached over and grabbed the front of his coat, pulling him into the alley. The former sailor was thrown onto the ground, and he looked up to the face of the infamous Dean Winchester.

The pirate held his sword against Castiel's throat, staring down at the sailor. Castiel's hand inched towards his own blade, though his eyes remained trained on the infamous pirate.

"Ello," Dean said, smiling down at his prey, "now I assume you know me, so who are you, good sir?" The pirate tilted his head, watching as the man's eyes were wide, yet surprisingly calm.

"Um," Castiel glanced down at the blade pressed against his neck, "my name's Castiel."

"Hi Cas, can I call you Cas?" Dean smirked as he continued to watch the strange man under his blade.

"Uh, I don't really enjoy being called that," Castiel answered, his hand now wrapped around the hilt of his blade.

Dean shrugged and pursed his lips, "Cas it is," he was silent for a bit as they both stared at each other.

It was then that Castiel unsheathed his sword and lashed out at Dean, who jumped out of the way. Castiel rushed up to his feet, sword now ready in his hand as he faced the Winchester.

Dean smiled slightly, but now he was excited, the adrenaline pumping through him as he locked eyes with Cas.

"Not bad, Cas. You do this often?" Dean wiggled his eyebrows a bit, and almost laughed as Castiel tilted his head in confusion.

"If your asking if I try to capture infamous pirates such as yourself, then no."

Dean shrugged, "Just trying to make small talk." The Winchester thrusted his blade forward, Castiel blocked and soon they were a dance of calculated steps and blows. They were weaving through the alley, until Dean managed to force Castiel into an abandoned shop.

Once again they were a whirlwind of swords, until Cas caught Dean off, and he managed to land a small blow on the pirate's leg, slicing through his flesh. Dean cursed, but Castiel maintained his advantage, and finally with the flick of his blade he cast out Dean's sword from his hand. He held his blade near the infamous Winchester, confidence in his eyes. But Dean's eyes were also confident as he pulled out a gun.

Cas lowered his blade, frowning. "You cheated."

Dean smirked, holding the gun level while he tried to stay off his injured leg.

"Pirate."


	2. Chasing Idols

**Wow! Can honestly say I was surprised and pleased by the initial reaction, thank you guys ^_^ A special thanks as well to Air Guitar Pixie and ****DeerTopus C. VonZenhousen** **for reviewing!**

_He held his blade near the infamous Winchester, confidence in his eyes. But Dean's eyes were also confident as he pulled out a gun. _

_Cas lowered his blade, frowning. "You cheated."_

_Dean smirked, holding the gun level while he tried to stay off his injured leg._

"_Pirate."_

* * *

Dean flicked the gun to his left, "toss the blade Cas," he ordered as he smirked, the pirate seemed to glow with confidence now that he was controlling the situation. Grudgingly Castiel obeyed, throwing his sword off to to his right.

"What are you doing here in Darton, Winchester?" Castiel asked as he stared down the gun in Dean's hand, his heart pounding in his chest.

"I'm here on business, you know. Being a pirate isn't all women and badassery," Dean squints his eyes and his grin widens a bit, "well at least not all the time." Castiel frowns at this, but Dean now walks back towards the door slowly, his pistol still trained on Castiel.

"Well Cas, I've had a grand old time with you. Now I don't make it a habit to kill pretty boy swordsmen, so I think it's time I make my leave." And with a tip of his hat the infamous Winchester turned towards the door and ran out.

Castiel quickly grabbed his sword that had been lying nearby, and rushed to the door. He reached for the doorknob, but the door wouldn't budge. Several times the sailor tried to open the door, until finally he began to throw himself against it. After several tries, the door gave way, and Cas landed painfully in his side back into the alley where his troubles had started.

He ran towards the crowded street, and desperately searched for the hat he had spotted not too long ago. His eyes scanned the people, but after not one sight of the hat he gave a growl of frustration and kicked one of many barrels strung across the alley. Castiel cursed, running one of his hands through his hair while he sheathed his sword angrily.

_Pretty boy swordsmen, _Castiel snorted at the thought, _I'm going to find that fool._

* * *

Dean watched slightly afar at all the sailors buzzing about the port, leaning casually against a wall in an alley. He glanced down at his injured leg, he had managed to wrap it and was pleased that it wasn't severe. His eyes then began to take in all of the lovely ships, until a particular one caught his eye.

"There you are, baby." Dean muttered under his breath, his eyes now locked onto a particular sleek looking black ship. With a destination now set he got up from his previous position of leaning against the old building, and he began to make his way through the darkness of the various, crisscrossing alleyways he traveled through. He frowned, knowing he had to be careful now after his little meeting with Cas.

_He was quite charming_, Dean thought jokingly; smiling now as he remembered their confrontation that had only occurred a bit ago. Finally Winchester found the right building he was looking for, and he knocked on the back door forcefully with his fist.

"Bobby!" He shouted, and he heard the old fool curse as he eventually opened the door. Dean looked at the man, taking in his scruffy red and grey beard, and it wasn't hard to smell the alcohol that Bobby seemed to be soaked in.

"Hey boy," Bobby greeted, and he opened the door to make room for the pirate. Dean nodded towards Bobby as he stepped into the old house, it seemed to be in the same condition as the owner itself. The Winchester took off his hat and looked around the place before sitting down on a wooden stool, his eyes still sweeping around the house.

"So, Bobby," Dean began after the old man sat down across from him, " looks like you were right after all. She's here all right."

"Course I'm right idjit," Bobby replied before taking a sip of his drink, " don't you know I would've checked before letting you know?"

Dean smiled, a small chuckle escaping him after hearing Bobby. But his face grew a bit serious, and he looked at Bobby with a fierce look in his eyes.

"Do you have any new information on him?"

Bobby sighed, taking a moment to drink once more from the mug in his hand. He set the glass down and rested his hands on his stomach, his fingers intertwined.

"I've got a name for the ship he's on," Dean almost stood up with excitement, but something in Bobby's tone made him stay seated.

"And?" Dean asked while Bobby had remained quiet after his news.

"It's the _Hellhound,_ Dean." The old man watched as the pirate's whole body seemed to freeze, Dean's jaw clenched as he closed his eyes. He almost immediately began to shake with anger, but he took a deep breath, and after several more he opened his eyes to look at Bobby.

"That son of a bitch," Dean muttered as he stood up and paced across the room, "of course it's the friggin _Hellhound_!" He stopped, hands on his hips as he looked down. His mind was racing as he tried to think of something, anything. But he shook his head, and walked back over to his chair before sitting back down with anger still burning in his eyes.

"So," Bobby said after watching Dean's reaction, "any plans on how you're going to get the _Impala_?"

"When there's a will there's a way Bobby, I'll figure out something and try to get out of here by tonight with her."

"Tonight? That's a little fast don't you think?"

"Well I kind of got made earlier by this one guy, but I managed to dodge him in the end."

Bobby frowned, "Happen to catch his name?"

"Name was Castiel," Dean replied, and watched as Bobby was now the one to begin to panic. The old man's eyes grew wide and he sat up, leaning forward in his chair now towards Dean.

"Boy, you just pissed off a former high-ranking sailor for the Royal Navy, you know what he's gonna do now that he knows you're here?"

It was then that Bobby and Dean both heard the ringing of the town bell, Bobby filled with dread when it rang five times.

"He must have alerted the guards that you were here," Bobby said as he now stood up and looked around the room before staring at Dean, "you need to get out of Darton now, boy. Trust me, these soldiers are thorough, and it's best if you're out of the town while they search."

Dean nodded, and quickly embraced Bobby, "thanks," he whispered to the old man before placing his hat back upon his head and racing out the door, Bobby watching as the pirate left.

"Good luck, Boy." He muttered before he sat back down and took a long sip of his drink.

* * *

Castiel thought hard, sitting once more by the beach after alerting the guards that Dean Winchester was in town. He couldn't help but smile a bit, he had enjoyed letting them know because they were rather _thorough_ when it came to pirates; if Dean hadn't left town then he would surely be captured by the guards.

But Castiel decided he wasn't satisfied, he kept thinking about Dean and his encounter, the incident replaying in his mind.

"Pretty boy my ass," he growled and quickly got up before looking at the town.

_The alleyways, _Castiel thought while his head naturally tilted a bit as he thought, _that's where I would go to avoid attention_.

Castiel rushed to the town, he couldn't help but feel excited at the thought of capturing the infamous pirate. Finally he wouldn't have to the be the outcast, the sailor stuck on the land with the rest of these civilians when he should be out on the sea.

The former sailor weaved and raced through the alleyways, his eyes trained and focused in the darkness for any sign of humanity. Mentally he was doing his best to remember where he was, Castiel was searching just like the rest of the Royal Guards.

And he would find Dean Winchester, his heart was set on it.

* * *

Dean cursed as he crouched in the shadows the alleyway provided, observing the bustling crowd and the guards that weaved their way through the street and its people. He was at the home stretch, all he had to do was cross this road and he would be free of Darton until the alert died down, and then he could fetch his prize.

The Winchester glanced behind him, suddenly feeling a bit open from behind him, but there was no one there so he sighed and once again watched the street.

It was then that a guard noticed him, a young fellow whose eyes were bright and wide when he had spotted the Winchester.

"Damn it," Dean muttered as he turned and raced back into the web of alleyways, listening now as whistles were blown and footsteps were now following him.

"Not good, not good, not good," Dean kept muttering as he took turns and knocked over barrels behind him to try and slow the guards down. He took a sharp left, only to see a surprised Castiel. They both froze at the sight of one another.

"Oh come on, you again?" Dean shouted before turning around and racing back into the maze. He glanced behind him to see now that Cas was tailing him as well, and he growled.

"Really not good, really not good," he now muttered to himself.

Dean's eyes scanned for a way out, and then he noticed a nice little set of barrels that were stacked high enough to reach the roof, as well as staircase like. He risked one more glance at Cas, and couldn't help but smirk at the former sailor before he began to climb up the barrels.

Just as Dean made it to the top Castiel had begun to climb up the barrels himself, but Dean was a step ahead of the raven-haired man. He shoved the barrels, knocking a few over a long with Castiel who went down with them. Dean watched as the former sailor landed on his back, and managed to roll out of the way just as Dean launched another barrel at him.

The former sailor glared at Dean, who tipped his hat to the man, a grin on his face.

"It's been fun, pretty boy." Dean winked and turned around, and began to race across the rooftops. He tried to ignore the now stubbornly close whistles of both officers in the alleyways and those on the main street who caught a glimpse of the pirate on the roof.

Dean sprinted and jumped from one building to another, trying to stay ahead of the guards that were slowly surrounding him. His heart was pounding, the noise was almost consuming the rest of his hearing. He jumped once more onto another building, nearing the edge of town again. He ran to the edge of the building and froze. The next building was a bit of a distance, definitely greater than his previous jumping feats. Hesitantly Dean approached the very edge, and almost jumped at the sound of shouting guards. The pirate looked around and cursed, seeing that they too were on the roofs, and they were approaching fast. Dean stared at the distance once more, worry in his eyes as he tried to make a decision.

"Oh screw it," he growled, taking a few steps back before launching himself off the rooftop, reaching out for the next building's edge.

His hand grazed the wall.

**Aren't cliffhangers (almost quite literally) great? I hope you enjoyed this chapter and I hope to post the next one in the near future! Reviews and the like are appreciated greatly!**


	3. Darton's Heavenly Host

**Salutations readers! Quite the cliffhanger we had last chapter, no? ;) Anyways, thank you Air Guitar Pixie, Kather Swine, McGowanG602, ****fictionfairytalesfantasy4921** **and DeerTopus C. VonZenhousen for reviewing, you guys make me feel all warm and fuzzy inside :3 Well now lets see what will happen to our infamous pirate now, shall we?**

_Dean stared at the distance once more, worry in his eyes as he tried to make a decision._

"_Oh screw it," he growled, taking a few steps back before launching himself off the rooftop, reaching out for the next building's edge._

_His hand grazed the wall._

* * *

Dean's eyes grew wide as his hand was unable to fully grasp the ledge, and he began to drop down towards the alleyway.

"Son of a bitch!" Dean managed to shout while he plummeted, until he landed into one of the many dark paths that formed the maze of alleyways.

His injured leg screamed as his mind tried to register the inner panic inside of him. He noticed his hat laying beside him, he slowly reached over and picked it up, before trying to sit up. His body shouted angrily at him in protest, as if he had been in a dozen fist fights in one go. He had managed to get to his feet when the first of many guards came.

"Halt!" The guard shouted, his sword out and his eyes slightly wild with excitement and fear at the sight of the infamous Winchester before him. Dean looked at the guard, an arm wrapped around his side as he leaned against the wall. He stared down the soldier, who began to grow nervous, shuffling his feet.

It was then that Dean used the arm that was hugging his side to lash out with his sword, he had made sure to reach for it when the royal officer had approached. Once more his body was red with pain, but the adrenaline began to carry him as he easily overpowered the soldier.

Quickly Dean turned and paced through the alleyways, his arm still wrapped around his side while he gripped his trusty blade tightly. As he turned left he was met by a group of guards, who were startled for only a moment before they charged.

"Damn, they just don't quit," Winchester muttered before turning and racing back through the labyrinth, but the more turns he took the more officers he encountered.

Finally Dean was trapped, royal guards blocking both of his exit points. He stood his ground, eyes burning as his gaze swept across the many that had gathered. He took in every emotion the collective group seemed to give off, smiling slightly at their fear but that was but a small number. The rest were confident now, knowing that he was cornered and could no longer dodge the inevitable.

"Well, Mr. Winchester, how long has it been?" A cynical voice called out from Dean's left. He turned his head slowly and watched as the soldiers made way for the owner of the scornful tone.

"Zachariah," Dean growled as the older man now stood near, Zachariah smiled as he took in the injured form of Dean Winchester. He took a step closer, but Dean raised his sword in warning. The pirate watched though as the various soldiers also raised their own blades, and Zachariah's grin grew.

"Now Dean, I am rather curious as to why you are in Darton, but I'm sure you can tell me all about it once we head back to the prison, right kiddo?" Zachariah's eyes were wide with delight and confidence at the sight of the weakened Winchester.

"Go to Hell," Dean managed to utter, he was starting to get dizzy from standing up for so long, not to mention the current pain in his side that was all too noticeable among the officers.

But Dean was angry, and especially pissed off at the sight of Zachariah. Rage bubbled and boiled inside of him. With a growl he lashed out with his sword towards the older man.

* * *

Castiel watched the encounter as he crouched behind a group of barrels. The former sailor was surprised when he heard Dean and Zachariah, the fact that they even knew each other Castiel found rather astonishing.

But his eyes widened greatly at the sight of Dean Winchester as the pirate swung his blade at the head of the guard.

However, the attack ended as soon as it started. With just a flick of his own sword, Zachariah managed to block the attack and toss the sword out of Dean's hand with startling speed and power.

"Please, Dean. At least have the decency to show me some respect," Castiel heard Zachariah say as the leader slowly walked up to Dean. The pirate held his ground, his eyes still narrowed at the older swordsman.

"Well, you can take your respect and stick it where the sun don't shine," Dean replied, he managed to smirk as he stared down Zachariah. They were so close to one another now, Zachariah's face only inches from Dean's. Castiel's heart was beating, he didn't realize how tense he was until he noticed how white his knuckles were from his grip on one of the barrels.

It became a silence that was completely unbearable as both entities on the battlefield locked eyes, the spectators all awaiting for the next move to be made.

Castiel watched, his eyes growing even wider as one of the two made their move.

* * *

Dean wanted to strangle Zachariah from the moment he approached him. Now the two were silent, trying to analyze the other in the deafening silence. The only noise Dean could hear was that of his own heartbeat, and the heavy breaths that he drew. He was too weak now to do much, as much as he wanted to take a swing, he just didn't have the energy. The adrenaline had already left, his body left tired and defenseless when Zachariah had approached.

So when the older of the two swung his fist into Dean's stomach, the pirate couldn't help but crumple and fall to the ground on his back. While trying to breath, Dean tried to reach for his own pistol but was stopped short as a black boot fell onto his wrist, crushing it against the cobblestone ground. He considered reaching with his other hand, but Zachariah's face was now serious as he placed the tip of his sword against Dean's throat.

"Stay down, _pirate,"_ Zachariah spit out the last word, a look of victory dancing in his eyes. The leader looked up at his soldiers, and he pointed to two of them.

"Gabriel, Thaddeus. Secure this man and take him away," Zachariah turned to face all of those under his command, "good work, everyone. Darton is safe once more!" The soldiers cheered and Zachariah smiled down at Dean.

"We'll talk later," he whispered, he leaned over and grabbed Dean's pistol from his holster before Thaddeus and Gabriel walked over to the defeated pirate. The two pulled Dean up to his knees, he struggled but they managed to bring his hands behind his back. Dean's eyes scanned the crowded soldiers in the alley, but then he noticed a particular former sailor near a group of barrels. The two locked eyes, Dean's green staring into Cas's vibrant blue. So, even after getting the crap beaten out of him, Dean tried to lighten his own mood slightly now that he spotted the former sailor.

Dean winked at the former sailor before he was pulled to his feet and lead away by the two soldiers.

* * *

Castiel was surprised when Dean Winchester managed to spot him from his hiding place. but when the pirate winked at him, Castiel's confusion outweighed his earlier surprise. He watched as the pirate smirked at Castiel before he was lead out of the alleyway, stumbling a bit while he tried to keep up with the guards.

Waiting until the rest of the guards had left, Castiel left his hiding place behind the barrels and returned to the crowded street once more. He looked around, hearing the bits and pieces of conversation that everyone was talking about; the arrest of Dean Winchester. Thoughts of the pirate began to crowd Castiel's head, he quickly shook his head to rid himself of them. But they kept coming, kept bothering him and prodding his curiosity.

Sighing, Castiel shook his head before deciding that he couldn't keep himself sane unless he at least attempted to talk to the pirate. With a destination set, Castiel began to make his way through the crowd, the image of green eyes burned into his eyes.

* * *

Dean pulled and struggled slightly against the two soldiers who had walked him to the prison, repeatedly tugging his arms against their iron grip. Deep down though Dean welcomed their hold, it was hard enough for him to stay on his feet, let alone walk.

"Lovely weather we're having boys, right?" Dean remarked to the guards, but they remained silent. The one on his left tightened their grip slightly, and Dean grinned.

"Well aren't you two just a couple rays of sunshine," Dean continued, watching as the two looked at each other before repeating their silence to Dean's conversation.

"So, what's it like to be one of Zachariah's little soldiers?" Now both of their grips tightened, their pace increased and Dean had to focus a bit on keeping his feet moving right along with them.

"You know I'd go far as to say he thinks of all of you as his-"

"Shut your trap you-you excuse for a human being!" The guard on his left, Thaddeus, shouted as he interrupted Dean. Gabriel shot a look at Thaddeus who looked down, but only after glaring at the Winchester, his hand clenched so tightly that his knuckles were a pale white.

"Excuse for a human being, eh? Funny, I don't get that as often as you would think," Dean replied to Thaddeus, his eyes now danced with a glint of mischief to help replace the look of pain.

They soon stopped in front of a rather gray building, the outer walls dreary like, the building almost seemed to sag at the corners. Thaddeus let go of Dean and walked up to the door, searching on his key ring for the the right one to unlock it. Dean observed the building, taking count of the lack of windows on the front.

"Can I have the honeymoon suite?" Dean remarked to the guard on his right, Gabriel, who shook his head slightly, Dean was able to catch the small smile on the guard's face.

"Sorry, that room is occupied," Gabriel replied to the pirate, who smiled when the soldier had answered.

"Well that's a shame," Dean continued.

"Guess you'll just have to live with the normal rooms like the rest," Gabriel ended, and he led Dean through the now open door, Thaddeus taking his position back on Dean's right.

There were some calls, remarks, and laughter coming from the fellow prisoners as they saw Dean Winchester walk in. But Dean just smiled and chuckled quietly to himself. They stopped in front of an empty cell, and Thaddeus stepped up once more to open the door. Dean looked all around, trying to notice all the small details. With a click Dean focused his attention back onto the cell as Thaddeus opened it. The guard walked over to Dean and finally released his hands from behind him

Harshly, Thaddeus shoved Dean into the cell. Dean rubbed his wrists as he looked at the two guards.

"It's been a pleasure boys," he smiled at the two. With narrowed eyes Thaddeus walked away, but Gabriel stayed a moment. He stared at the Winchester, who watched in curiosity as the guard smiled slightly.

"See ya around, Winchester," Gabriel finally stated as he turned and strolled out of the prison, humming.

Dean snickered, after Gabriel's departure; the guard had grown on him. He turned slowly and looked around his cell, a wall to his left made of solid cobblestone. Quickly Dean shed his overcoat and hat before he examined the wall, looking at the window that sat in its center. The pirate walked over and tugged on the bars, and he noted that a couple were rather loose.

"Lucky me for getting the corner office," Dean whispered to himself, and he began to twist and pull at a couple of the bars. Some moved easily, while others were a bit stubborn. He turned around and looked around the room, trying to find anything that would help. Then his eyes spotted it, a small pile of smooth, jagged rocks lying under the excuse for a bed.

He walked over and squatted down before he began to sift through the pile to find an ideal tool. After checking most he found one that seemed to fit the requirements.

"Now I feel bad for the son of a bitch who didn't get to finish his own escape," Dean muttered as he began to walk back towards the window. But the pirate froze at the sound of the door to the prison open, he quickly walked over to where his coat lay and placed the stone in the inner pocket.

Grabbing his hat, Dean sat down against the wall and placed the hat over his head, covering some of his face. As he sat down, Dean couldn't help but sigh, his body still ached and he felt relieved to take the opportunity to pause on his great escape.

He listened, counting the echoing steps of the person who had entered the prison. They grew louder and louder as they began to approach the very last cell, Dean's own cell. Finally they silenced after stopping in front of him.

Dean glanced out through the corner of his eye, and he couldn't help but grin at the sight of tan.

"Just can't keep away, can you pretty boy?"

**End of chapter three, yay! I kind of had a bit of trouble writing this one, but I got to end it the way I wanted to so it's a success in my eyes! Thank you for reading and I hope to release the next chapter soon :)**


	4. The Prison Questionnaire

**Hi, welcome back for another installment of Pirates! Thank you Akayuki Sawada, Kather-Swine, Air Guitar Pixie, McGowanG602, and ****DeerTopus C. VonZenhousen** **for reviewing! A thanks as well to those who have favorited and followed this story, you guys are great! And with that, let's get started, shall we?**

_He listened, counting the echoing steps of the person who had entered the prison. They grew louder and louder as they began to approach the very last cell, Dean's own cell. Finally they silenced after stopping in front of him._

_Dean glanced out through the corner of his eye, and he couldn't help but grin at the sight of tan._

"_Just can't keep away, can you pretty boy?"_

* * *

Dean tipped his hat up and faced the former sailor that stood before him. His gaze was drawn towards Castiel's blue eyes which were watching the pirate with an intense look within them.

"Your 'pretty boy' remarks are not entertaining, Winchester," Castiel replied to Dean's previous greeting for the former sailor.

"Just having a bit of fun, Cas." Dean smiled before jumping up to his feet, walking up to the bars that separated him and the blue-eyed man.

"So," Dean continued, his hands wrapped around the bars as he and Castiel continued to stare one another down, "what can I do for you Cas?"

Dean's smile grew at the sight of Castiel frowning at the mention of the pirate's nickname for him.

"Why are you here in Darton?" Castiel asked, he turned away from Dean and began to look around the prison along with the inside of Dean's cell.

"Antiquing," Dean remarked sarcastically. He enjoyed the look on Castiel's face as the former sailor turned to look back at Dean; his face both annoyed and confused, "what's it to you?"

* * *

Castiel frowned at Dean, he could never understand this man's sense of humor.

"I would appreciate an honest answer, Dean." Castiel tried, his voice low while he stared at the pirate, his face showing his annoyance of the Winchester's sarcasm.

The pirate raised an eyebrow at him. "Again, what's it to you Cas?"

Castiel sighed, and the two stared at each other for a bit before another question crossed Castiel's mind.

"How do you know Zachariah?" Castiel watched as Dean's face went rigid, the pirate clenched his jaw and his eyebrows drew closer together at the sound of Zachariah's name.

"Long story, pretty boy."

"Winchester stop calling me a 'pretty boy' damn it!" Castiel shouted, and Dean's face immediately went into a look of surprise before he relaxed and chuckled at the former sailor's reaction. He raised his hands in mock surrender.

"Sorry Cas, didn't know you were so insulted by your looks," Dean wiggled his eyebrows slightly at the former sailor. Cas narrowed his eyes at the Winchester.

_This man is insane!_ Castiel shook his head, _why did he have to be curious about a man who can't even answer a single question? _

_Because he's the infamous pirate, Dean Winchester_. _He's the one who sailed the seas with his loyal crew and beloved ship that was darker than shadows,_ Cas replied to himself. Castiel looked back up towards the pirate, who was watching with curiosity while Cas thought to himself. It was then that the pieces were placed, and the puzzle was complete.

"You're here for the _Impala,_ aren't you Winchester?"

* * *

Dean frowned, trying to hide his surprise after Castiel mentioned his baby. "What do you know of the _Impala_, Cas?" Dean asked, he was intrigued now. Castiel had just become a lot more interesting to the Winchester.

"Plenty, she was claimed by her Highness after being captured from a pirate crew a couple months ago. Now she's here and getting ready to join up with a few others for the exploration of the Sasnak Islands."

"Sasnak Islands, huh? Well good luck to the sailors. Place is filled with all sorts of things, very hard to last long there before you end up missing a limb or two."

Dean watched as Castiel's eyes lit up with surprise and wonder.

"You've been to the Sasnak Islands? I thought that it had yet to be truly explored."

Dean snorted at the former sailor, "get with the times pret-" he paused when he noticed the look in Castiel's eyes; he couldn't upset the former sailor again right now, "Cas. Now back to the _Impala-"_

Castiel interrupted once more, realizing what the pirate was doing. "Dean Winchester, if you think you are getting out of this prison and can take the _Impala _single-handedly, then you truly are insane."

Dean smiled innocently, "I've said no such thing about escape. I was just curious about the ship, lovely thing isn't she?"

Dean watched as Castiel nodded absent-mindedly. The pirate cursed himself for not being able to see if Castiel knew anything more about his ship.

"Is it true?" Dean was pulled out of his thoughts as Cas asked him a question.

"What's true, Cas?"

"The _Impala,_ that was your ship, wasn't it?"

* * *

Castiel waited for an answer, looking at the Winchester with a raised eyebrow, he noticed that he had even tilted his head when he asked the question. Castiel chastised himself mentally, he finds himself doing that too often these days. But he was brought back to reality when Dean surprisingly replied to him.

"That's a possibility. What's your last name Cas?" Castiel's brow furrowed at the pirate's question.

"Why would you even want to know that?" Castiel asked, his eyes squinted slightly as he stared at the Winchester in curiosity once more.

"Oh come on Cas, you know mine. It's only fair if I know yours too, right?"

"You are a strange man, Dean Winchester."

"Just humor me, Cas."

Castiel sighed, pinching the bridge of his nose while he talked to the pirate. How he tolerated this conversation Castiel will never understand. With a sigh, he closed his eyes and replied to the expectant Dean.

"Novak, the name's Castiel Novak." He opened one of his eyes to see Dean staring at him, the pirate's face serious and focused in thought. Castiel managed to hear Dean as the pirate muttered to himself.

"Novak, of course it's Novak," Dean shook his head and chuckled quietly, all the while Castiel watched with one of his eyebrows raised once more as a sign of curiosity.

Dean smiled at Castiel, "Castiel Novak, and you were a sailor," the pirate pursed his lips slightly and nodded to himself before he got up from his position by the door.

"Well Cas, this has been fun. But after falling from a rooftop and all this chit-chat, I need to catch up on my beauty rest." He winked at the former sailor, "maybe we can talk again sometime." Cas watched as the pirate then elegantly fell onto his bed, covering his face with his old, dark hat.

Castiel shook his head after he found himself smiling at the sight of the sleeping Winchester. He cleared his throat slightly, and rolled his shoulders back before beginning to make his way back to the way out of the prison.

He stopped though, and knocked on a wooden door to his right that lay only a few yards from the exit. He watched and listened as someone walked over and opened the door, turning the knob.

He looked down at the person who opened the door and was met with warm, honey-amber eyes.

"Hello, Gabriel," Castiel greeted his older brother, who was surprised to see the taller of the two.

"Cassie!" Gabriel smiled and hugged him, it took Castiel a moment before hugging his brother back; he wasn't used to receiving many hugs.

"Who let you in this time?" Gabriel asked as he invited Castiel into his living quarters.

"Theo," Castiel replied as he looked around his brother's room. He noticed the various sweets that coated Gabriel's counters. He watched as Gabriel picked up a bag of confections.

"Not surprised. You should try these, they're candied orange slices. I just got these from Ms. Tate, she misses you by the way. You should visit her soon," Castiel turned down the sweets, watching as his brother popped a couple in his mouth.

"It is amazing your teeth haven't rotted away yet," Castiel commented. Gabriel smirked, "everyone has their beauty secrets," the elder brother replied before seating himself by his fireplace.

"So Cassie, what made you want to drop by the neighborhood?"

Castiel pulled out a wooden stool from his brother's table and sat across from Gabriel.

"Dean Winchester," Castiel answered. Once again Gabriel smirked, raising an eyebrow.

"Ah, the great and infamous Mr. Winchester. Quite the character, isn't he? He managed to piss of Thaddeus pretty good on his stroll over here."

Castiel nodded, easily able to understand why the officer would become so enraged because of the pirate. Gabriel's next question brought back Castiel's attention.

"So, why the curiosity with the ray of sunshine?" Castiel sighed before telling Gabriel of his first encounter with Dean, and then of his previous conversation with the Winchester.

"What I want to know," Castiel began, "is why he thinks he could try and take a ship all by himself. Also, how he and Zachariah happen to know each other. I don't know Gabriel, things have been getting all tangled in the Royal Service, I'm almost glad I was discharged so I could escape the growing turmoil." Castiel sighed and shook his head, he rubbed his temples slightly to try and calm the inner storm of thoughts that was happening in his mind. He looked around the room and noticed a particular blade and pistol almost hidden within Gabriel's collection of sweets.

"Are those his?" The former sailor asked.

"Yup," Gabriel nodded, "Zachariah had me take them and I didn't really have a place to put them so.."

Castiel stood up and walked over to the counter. He picked up and examined the blade, he couldn't help but admire the great craftsmanship of the sword; it was well made and taken care of.

Next he examined the pistol, it wasn't special or unique in any particular manner. He placed them back down and closed his eyes. Dean Winchester was everywhere he went, even at his brother's.

"I should probably go," Castiel spoke with a quiet voice to his own surprise. Gabriel nodded and smiled warmly his brother.

"Drop by more often, okay? And try to catch up on the finer things in life that you haven't appreciated yet. You seem like you could use a bit of R&R." Gabriel pulled his taller, younger brother into an embrace which Castiel returned.

Castiel sighed as he left the prison, the crowded street now with plenty of room thanks to the growing darkness of the approaching night. The moon was almost full as Castiel looked up to examine it. The stars had yet to truly come out, so the former sailor ended his star gazing and began to make his way back to his own home.

Castiel was almost across the rest of the street when he stopped at the sound of his brother.

"Castiel, Castiel!" Gabriel shouted. Castiel rushed to his brother, noticing that he held Dean's confiscated weapons.

"What is it Gabriel?" The former sailor asked, searching his brother's eyes for any hints as to why he was called.

"It's Winchester. He's escaped."

**Well this was a fun chapter to write ^_^ Thank you all for reading, I really appreciate the email alerts I receive because of you guys! Please feel free to review, follow or favorite if you want to, and I'll try to get the new chapter out ASAP now that things are getting even more exciting :D**


	5. A Pirate's Reunion

**Hi! Thanks to Air Guitar Pixie, DeerTopus C. VonZenHousen, Akayuki Sawada, fictionfairytalesfantasy4921, and all of you who have decided to follow and favorite this story! I appreciate this in the most sincerest of ways and do believe that you are the driving force for me to enjoy writing more chapters, because I enjoy where the story is going and I'm happy to know that I'm not alone. Thank you guys so much for your continued support, and now back to our favorite infamous pirate everyone!**

_Castiel was almost across the rest of the street when he stopped at the sound of his brother._

"_Castiel, Castiel!" Gabriel shouted. Castiel rushed to his brother, noticing that he held Dean's confiscated weapons._

"_What is it Gabriel?" The former sailor asked, searching his brother's eyes for any hints as to why he was called._

"_It's Winchester. He's escaped."_

* * *

As much as Dean wanted to, he knew he needed to seek out Bobby before he could take back his ship. He raced through the alleyways once more, time wasn't on his side as he assumed that the guards would be alerted once more.

Finally Dean found the familiar back house, and he banged on the door.

"Bobby, it's Dean." The pirate waited as the older man opened the door, and he breathed a sigh of relief.

Dean walked into the house and Bobby embraced the Winchester tightly. Dean hugged him back, allowing himself to slow down and relax for a moment.

"I thought they got you, boy." Bobby said as he held onto Dean by his shoulders.

"They did, Bobby. But I'm out and I need to hurry. How fast will it take you to call in everybody?"

"It shouldn't take long, what do you mean they had you?" Bobby searched through the various pieces of paper on his table while he talked to Dean.

"As in I fell off a roof, Zachariah showed up and I got arrested. I even got a visitor," Dean replied looking towards the door occasionally. Bobby stopped his search and looked at Dean.

"Kid, you just can't go anywhere without running into trouble, can you?"

Dean smiled at Bobby, "that seems to be the case, Bobby."

The older man shook his head and walked over to his window, giving a low whistle. He turned back towards Dean.

"Who was your visitor?"

Dean shook his head, a chuckle escaping him.

"You never told me that Castiel was a member of the Novak family. Imagine my surprise to hear that he's not only a Novak, but he was also a sailor! Strange how the universe works, don't you think?"

"The Novaks are a big family, Dean." Bobby paused after hearing a reply to his whistle, a higher-pitched call returning his original message. He whistled a tune out of the window and faced Dean.

"They should be making their way to her now, you best get going you idjit. Lord knows what trouble you'll run into out there if you don't get a move on."

Dean laughed before walking over to Bobby and hugging the elder man once more, his embrace fierce and tight.

"Thank you Bobby, for everything." Bobby wrapped his arms around the pirate, allowing himself to smile.

"Yeah kid, just promise me you'll find him and never let him out of your sight, got it?" They let go of the embrace, Bobby's hands now holding Dean's shoulders.

"I'm gonna find him, Bobby. Don't worry," Dean answered, his eyes now full of confidence and determination.

Bobby nodded, and with one last squeeze he released the Winchester from his grip, and watched as the pirate raced out of the house for a second time.

* * *

Castiel and Gabriel raced through the town, trying to find the shortest way to the port.

Castiel growled in anger, "Who thought placing the prison and the port on opposite sides of the town would be a good idea?"

"Well at least we know where he's going, Cassie," Gabriel replied, the two pushing past the small crowds still gathered in the street. Eyes were drawn to the Novak brothers as they sprinted, curiosity bubbling inside the spectators.

"Do you know who's on guard at the port right now?" Castiel asked, his eyes focused on trying to find faster ways to the port.

"It should be Nathaniel and Neil on duty right now," Gabriel answered, keeping pace with Castiel.

"If only we could alert them," Castiel cursed, taking a sharp right into the alleyway. Gabriel bumped into the wall as he followed Castiel, trying to stay close to his younger brother. Castiel listened as his brother remained quiet. Purpose pushed him forward as he veered to the left, smiling as his brother cursed and ran against the wall, angered by the unexpected turn.

"No time to waste," Castiel called out to Gabriel and couldn't help but smile at the sound of his brother muttering under his breath.

* * *

Dean looked over the corner at the nearby peer, admiring his ship before focusing on the two guards that stood by the entrance. Multiple plans began to form in his mind, but he jumped as a hand gripped his shoulder.

"Son of a-" Dean began until a hand covered his mouth. The stranger pulled him back into the darkness of the alley before releasing him.

The Winchester turned to face his mystery attacker, but immediately dropped his stance at the sight of just who it was.

"Balthazar you ass," Dean whispered angrily at the man in the shadows, his smile sticking out among the darkness.

"Ello, Winchester; it's been awhile," Balthazar greeted, stepping out from his cover. He pulled the infamous pirate into a quick embrace. Dean smirked at the fellow pirate.

"That it has been. How's business?"

"Oh you know, full of drunks that keep it standing. But I've got a friend who's been eyeing the place for a bit now, they were surprised by my offer," Balthazar grinned once more as he shook his head slightly, "it's a miracle that you managed to find her again."

"Any sign of the others?" Dean asked, looking back towards the port once more.

"You should know that most of us jumped at the opportunity to sail again, keeping on the down low isn't really appealing, Winchester." Balthazar looked up towards the sky.

"Anyways most of us are around, just waiting for our fearless leader to arrive," Balthazar continued, his eyes dancing with happiness and anticipation. A smile formed on Dean's face at the sight, saving a retort that he was about to counter with.

"Well lets get this show on the road, shall we?" Dean asked, observing the empty street in front of him. The pirate smiled before whistling a well known song of the sea. His pitch bounced from low to high, and he watched as the guards looked around to try and find the creator of the tune.

Dean and Balthazar stood side-by-side, and they glanced at each other. After sharing one look, the two walked out of the darkness and into the moonlit street. Balthazar joined Dean in the tune, and together they walked down towards the pier. Dean's face brightened at the sound of another whistle joining them, and soon more gathered. A choir of whistles sang in the street, marching as one.

He glanced back and grinned at the sight, the crew reunited once more. He carried the tune even louder, until finally they stopped only a few yards from the tense guards. The soldiers eyes were wide as they stared down the reunited crew. The collected pirates' eyes were filled with nothing but joy and mischief as they stared down the last minor road block.

"Gentlemen," Dean greeted as he took off his hat and held it to his chest, "we've come to acquire our ship. Now you have two choices, let us pass. Or, if you are brave as you are stupid, you may try to stop us. No rush." Dean's eyes were bright and he smirked as the two soldiers looked to one another for consideration, he enjoyed the look of fear that gathered in the shorter one's eyes.

Dean nodded after silence was the only words spoken by the two guards.

"Well then, I believe a decision has been made," Dean faced Balthazar, "if you could deal with them, please."

Balthazar gave a small bow, "of course, Oh Great One.," his voice thick with sarcasm that melted with his accent. He signaled for a few of the others to assist him, and together they dragged the guards away,their hands and feet bound and gagged so as to not alert the others.

Dean turned to his gathered crew as he settled his hat back upon his head. He joined the others and their own smiles.

"Shall we?" Dean smirked and embraced the warm feelings that gathered inside of him. Sure his body still hurt like hell, but it had worked.

His family was reunited once more, and he embraced every feeling that gathered inside of him.

"All right, let's get her ready to sail!" Dean ordered, and the crew started to work, the captain watching from the pier as sailor after sailor began to head towards the _Impala_.

But Dean took a look back towards the street, and his eyebrows raised at the sight of a speeding coat of tan approaching.

* * *

Castiel and Gabriel were running down the center of the main street, Castiel's eyes locked on a particular pirate who stood on the nearing pier.

"Where's Nathaniel and Neil?" Castiel asked, drawing his blade as they ran.

"He must've taken care of them, only explanation as to why they aren't there. They're good soldiers," Gabriel answered, his own hand wrapped around the hilt of Dean's blade, the other on the Winchester's pistol.

Castiel's eyes narrowed, and he picked up his pace, pushing himself to go as fast as he could. Gabriel did his best to keep up with his younger brother, both of them now focused as they finally reached the pier.

Castiel listened as Dean whistled with a high-pitch, but the former sailor ignored him. He rushed up the pier ahead of Gabriel before jumping towards the pirate, his sword lashing out.

Dean managed to jump back, cursing at the close call and the lack of his own sword.

"Hello to you too, Cas," Dean greeted, Castiel stared at the tense pirate; Dean wary of the blade and Castiel's stance.

"What did you do to Nathaniel and Neil?" Castiel asked, his eyes boring into Dean's bright green orbs.

"Don't worry," Dean said as he took a step back from Castiel with a hand outstretched, "they're not dead. Not how I really like to roll on people who're just doing their job," he answered as he continued to back up as Castiel approached.

"You're coming with me, Winchester," Castiel ordered, his eyes fierce and confident as the pirate continued to back away from him.

Dean licked his lips, his eyes searching all around the pier until he looked behind Castiel and the features on his face relaxed.

Castiel began to turn around to see what Dean saw, but was interrupted as a blond-haired man with a goatee swung down from a rope on the ship the color of shadows, barreling into the former sailor.

* * *

Dean watched as the two rolled and tumbled on the pier, Castiel's sword having escaped from his hand after the stranger collided with him.

Finally the two came to a stop, and the younger Novak brother wrestled with the stranger. But the stranger rolled on top of Castiel, pinning his wrists above his head. The man who pinned the former sailor looked to Dean, a dazzling smile appearing on the strange man's face. The infamous pirate smiled and shook his head at the sight.

"Always with the dramatic entrances, Balthazar."

Balthazar's smile widened, "helped save your ass, you damsel in distress."

"My hero," Dean muttered, bending down and picking up Castiel's sword. He examined the blade as he walked over to Castiel.

Castiel turned his head the other way, and it was then that he noticed that Gabriel was unarmed, his face full with a look of being pissed off as a gun was held to his head. Castiel squinted as he looked at the man who stood behind his older brother.

"Bobby?" Dean and Castiel asked unanimously, Castiel frowned as he felt his cheeks redden slightly when he and the pirate shared the call.

Bobby glanced down at Castiel before talking to Dean. "We don't have time for formalities boy, the royal officers are on their way. You're lucky I made it here first."

"Thanks Bobby," Dean nodded before looking back down at the pinned former sailor. Balthazar kept his eyes trained on Castiel as he held the young man down. His voice was directed towards his captain as he maintained his hold on the man under him.

"What do you want to do about these two, Winchester?"

Dean was silent for a moment before he heard the beginnings of shouts gathering further up the large street. He cursed silently, his mind racing as he thought of what to do. Dean glanced once at Gabriel before his eyes landed on Castiel's own striking blue.

"We don't have time, take them on board and put them in the brig," Dean ordered before walking over to where Gabriel and Bobby stood, collecting his weapons from the older Novak's feet.

"Thanks for holding on to these," Dean said to the guard before turning around and walking back to his ship.

"Hurry it up!" The captain ordered as he got on board, watching his crew as they bustled about, loading the ship with supplies and preparing for take off.

"It feels good to be back," Dean whispered to himself, smiling as he ran a hand along one of the railings on the edge of his beloved ship.

**Okay, I believe this is officially one of my new favorite chapters that I've written now. I hope you enjoyed it as much as I did writing it, and I'll post the next chapter soon! I'm considering starting up a schedule for when I post, although my organizational skills could use some help. Review, follow, or favorite if you want to!**


	6. Familiar Family

**Well, love the buzz I received from last chapter! Thank you to Akayuki Sawada, Guests, DeerTopus C. VonZenHousen, Air Guitar Pixie, fictionfairytalesfantasy4921, and Kather-Swine for reviewing! A thank you also to those who have favorited and followed. Virtual hugs for all of you, now back to this old sea dog's tale!**

"_We don't have time, take them on board and put them in the brig," Dean ordered before walking over to where Gabriel and Bobby stood, collecting his weapons from the older Novak's feet._

"_Thanks for holding on to these," Dean said to the guard before turning around and walking back to his ship._

"_Hurry it up!" The captain ordered as he got on board, watching his crew as they bustled about, loading the ship with supplies and preparing for take off. _

"_It feels good to be back," Dean whispered to himself, smiling as he ran a hand along one of the railings on the edge of his beloved ship._

* * *

Castiel narrowed his eyes as Balthazar kept the former sailor pinned down. The pirate smiled down at Castiel, "nice to meet you," he greeted. The younger Novak brother watched worriedly as Bobby Singer followed behind a quiet Gabriel, the older brother looking towards his younger sibling with concern in his eyes.

After they passed, Balthazar began to get off Castiel, still keeping a firm hold on his wrists as he got off of the younger man. Castiel acted calmly, standing up along with Balthazar who now held his wrists behind his back with one hand; the other holding onto Castiel's shoulder. They took a couple of steps before Castiel acted.

Fluently the former sailor threw his head back, connecting with Balthazar's own skull. The pirate loosened his grip and Castiel took advantage, pulling his arms free. Bringing his right arm forward and swinging his elbow into the older man's chest.

Balthazar took a step back after the blow. The pirate held his ground, blocking the way out back into town. He went into a fighting stance, his eyes flicking quickly to the _Impala_ before looking at Castiel.

Castiel threw a punch, but Balthazar responded in time. He grabbed Castiel's fist with his right, and in turn brought back his own hand. His fist connected with Castiel's jaw, and the former sailor's head turned with the impact, stumbling. But the pirate wasn't finished.

He grabbed onto the former sailor's arm that he still held and twisted it, bringing it behind Castiel's back. Swiftly he knocked the younger Novak brother to his knees, and the pirate cuffed him on the head. Castiel was surprised by the blow at the back of his head, it wasn't meant to hurt him; in fact it was more like the pirate was scolding him.

"Moron," Balthazar muttered, pulling the former sailor to his feet and hurriedly pushing him up the ramp and on board the _Impala._ Castiel glanced up to see Dean standing by the wheel, the captain watching his crew. They locked eyes until Balthazar walked him through a stairway, across a spacious room, and down into the lower depths of the ship.

They arrived to what seemed to be the lowest level of the ship, and a set of iron bars formed two separate cells. Gabriel stood looking around the room until his eyes landed on Castiel and an annoyed Balthazar.

The pirate tossed Castiel into the cell with his brother, closing the door and relaxing after finally being free from the younger Novak. He sighed and rolled back his shoulders, gingerly touching where Castiel had headbutted him. He looked at the two and gave a small bow to the observing brothers.

"Gentlemen, welcome aboard one of the finest vessels that has sailed the sea," He smiled and his face scrunched together, although the playfulness in his eyes was still very noticeable, "enjoy your stay." With that, Balthazar turned around and closed the door, his ascent up the stairs echoing in the room until they gradually faded away.

Castiel faced his brother, whose expression was anything but pleased.

* * *

Dean watched as Balthazar returned to the main deck empty-handed, the man's attitude lighter and happier as he assisted the other crew members. The captain had witnessed his friend's quick brawl with Cas, pleased to see that the pirate could still handle himself quite well in combat.

Casting his eyes back towards the town, Dean watched with a pang of worry as he noticed a sea of lights gathered on the main street. A crowd of red and white formed, lights in their hands while they massed together; their size increasing as time hurriedly passed.

"Are we ready yet, Balthazar?" Dean shouted out to his first mate as his eyes remained trained onto the now immense crowd. Wide with worry now were the captain's eyes as the soldiers now charged towards the pier, like a swarm of lightning bugs they grew closer and closer as one giant mass of light and noise.

"Aye, Captain!" Balthazar replied, his voice fighting over the rest of the crew's chatter. He trained his attention onto what his captain was watching in the nearing distance. Dean frowned when he heard a growing laughter, looking away from the possible onslaught his eyes collected on Balthazar, who was laughing at the sight of the gathered assembly of royal officers.

"What's so funny?" Dean called down, his focus now divided between the en route soldiers and his first mate who was now trying to calm himself. He watched as the older pirate clenched his abdomen, collecting himself before he answered the captain.

"Pardon me, Winchester. It just never ceases to amaze me how much trouble you seem to be able to draw in every time." Dean stared at Balthazar, who chuckled to himself before shouting out an order to the crew. The captain shook his head, grinning at the man's answer, but he grew serious and turned his attention to his ship and crew.

"Ready the sails, it's time to leave this miserable town," Dean commanded, the authoritative tone in his voice crystal clear to his crew members. He appreciated the collective "yes sir," that the entirety of the band of pirates replied with.

Dean felt a wave of nostalgia as he watched his band of pirates work hard, everyone rushing about as excitement buzzed among them. Freedom was near, but so was the authority. As the captain continued to watch the crowd he began to make out faces, and he grimaced as he saw a particular face leading the charge.

"Captain," Dean look towards the voice that had called forth his attention back to the ship. He locked eyes with Balthazar, who was grinning even bigger than usual.

"We're good to go," Balthazar continued, his gaze flicking towards the royal officers now on the pier.

The first mate watched with delight dancing in his eyes as the captain cleared his throat before shouting out to his crew.

"All right you good for nothings, set sail!"

"Aye, Sir!" The crew responded loudly, and they watched as the breeze began to carry the sails. The ship slowly began to pull away from the pier just as the first of the mass of soldiers reached the ship just as Balthazar and a few of the others disconnected the ramp from the _Impala_; tossing it towards the sailors.

Dean watched as Zachariah reached where the boat had been, his eyes blazing as he locked on to the captain. With anger the leader shouted out to Dean Winchester and his receding figure.

"We're coming for you boy!" Dean smirked, and he grabbed the hat from his head, holding it high above him with a waving manner.

"I can't wait for the reunion!" The Winchester replied. Now the pirate captain's attention was focused on Zachariah as the man turned to face his army. With a pointed finger the older man focused the attention of the crowd onto him and the object of desire; the _Vessel_.

The ship sat proudly in the port, its sleek light form standing out in the darkness unlike the _Impala, _which was gradually melding more and more into the shadows.

"Prepare this ship!" Zachariah commanded before casting one more glance of ferocity onto the _Impala _and its captain, "You can't run forever Winchester!"

* * *

Gabriel looked at his brother, eyebrows raised in a questioning look. The older brother's arms were crossed, hugging his chest as they both stared for a moment. Words were being gathered by both of them, and Gabriel acted first.

"Well this is just how I wanted to spend my time," the sarcasm laced thick into his voice as he glanced around the small room. "Thoughts, Cassie?"

Castiel was seething, his older brother watched as the young Novak kicked the wooden boards on the side of the ship, throwing a couple of hits at the strong ship's walls as well. He turned back to face Gabriel, who noticed the beginnings of a bruise forming on his brother's jaw.

"Who'd you piss off this time?" Castiel raised an eyebrow before seeing that his brother was talking about his jaw. The former sailor touched it lightly before looking up.

"I tried to fight off that pirate who pinned me down earlier; tried to catch him by surprise."

"The one who made the grand entrance? Guess you're on a losing streak now, huh?" Castiel glared at his older sibling, who couldn't help but smirk. Gabriel stretched out on the bench that sat near the ship's wall, his back resting against the cold metal bars that formed their cage.

"Well, Grumpy, that was a great plan of yours. 'We don't have time to alert the guards,' you said, 'they'll be too slow because of their size'. I always knew you were the smart one out of the whole family."

Castiel's eyes narrowed at his laidback brother, whose hands now held the back of his head. Silence followed before Castiel's eyes dropped down to the floor, shuffling his feet as he thought to himself.

After the silence had settled, the younger brother sighed and took after Gabriel. He sat down on the floor, legs stretched out as he leaned back against the formation of bars.

"I'm sorry about this, Gabriel," he muttered, his eyes flicking around the room, everywhere but Gabriel's quiet form. His ears perked at the sound of his older brother releasing a sigh.

"It's okay Cassie. We're not dead yet," Castiel snorted and he turned his head towards his brother before tilting his head, his eyes squinting.

In his brother's hand was a small bag, and he watched as his brother reached into it before pulling out a couple of candied oranges. The older Novak stopped looking out the small window and back at his confused brother. Gabriel grew defensive.

"What, I just remembered I had them, okay?" Castiel's head remained at an angle as he continued to stare at his brother.

"You," he began slowly as he tried to process his brother's actions, "were just taken captive onto a pirate's ship, and you are now eating candied oranges in a cell."

Gabriel smiled sheepishly as he shrugged, "what can I say, everyone has their quirks, Cassie."

Castiel shook his head, a low chuckle rumbling from him as he rested his head back against the wall and looked up, "I don't think I'll ever understand your actions, Gabriel."

The two grew silent once more, save for Gabriel chewing on his precious sweets.

* * *

Dean's heart was pounding as he watched the port and the gradually fading mass of soldiers along with their esteemed leader. As soon as it was nothing but a speck, the captain released a breath he didn't know he had been holding. Already he was going to have someone breathing down his neck, trying to find him and his crew.

"Can't I catch a break, is that too much to ask?" the Winchester muttered to himself before looking back out towards the spacious sea ahead of him. His attention was pulled though as a voice called out from the deck.

"First day back and you're already staring off into oblivion captain?" His eyes chased the owner of the voice, and he grinned at the woman who stood before him, hands resting on her hips.

"Lots to process and plan, Charlie." Charlie made her ascent up the stairs before standing next to Dean, his grip relaxing on the wheel as she approached. The redhead joined him as they watched as some hustled about, while others began to talk to one another; sharing stories from their time away and the times recalled.

"It's like deja vu, in a good kind of way," Charlie said, rolling up the sleeves of her loose white shirt, "Especially Balthazar, the guy's practically glowing." The two watched as the first mate ran about, changing between chatting with his fellow pirates or ordering them around.

"Yeah," Dean agreed, his eyes following Balthazar's bustling form, "I think the pub thing just wasn't his scene."

"Oh it was," Charlie replied quickly, a grin appearing on her face, "you should've seen it during late nights; the things that man can make women do."

The pirate captain glanced at his companion, her eyes mischievous and distant as she recalled many images. Dean snorted and shook his head while trying to hide his smile, "down girl." She winked before giving a goofy smile.

"Are you going to address the rest of the crew?" the redhead asked. "You know, what you've been doing while you were gone?"

Dean's face fell slightly, he cleared his throat and his grip on the wheel tightened slightly.

"It's complicated. Charlie, could you get Balthazar to handle the wheel for a bit? I need to talk to Bobby."

The curiosity was blatant in the pirate's green eyes, but she nodded. "Aye, aye cappy," giving a fake salute she jumped down the staircase leading up to the wheel and searched out the active first mate.

Once more Dean sighed and released the wheel after noticing his white knuckles. Descending the staircase, the pirate captain made for his chambers. He held onto the doorknob for a moment, realizing how long it's been since he was last inside. Slowly his hand turned the knob.

**And that's all for today everybody! Thank you for reading, and I'll try to bring more chapters out ASAP! Please review, favorite, and follow if you want to :)**


	7. Opening Doors

**Ahhh, here we are once more, back for another installment of Pirates! I'm looking at these reviews and can see that you all keep asking for a certain younger brother ;) Well, don't worry your pretty little heads; Sammy will definitely be in this story! I won't spoil the fun though for you about his own whereabouts just yet. Thank you to Kather-Swine(Happy Belated B-Day!), Deer Topus C. VonZenHousen, Akayuki Sawada, fictionfairytalesfantasy4921, Air Guitar Pixie, and Daughter of Rhea for reviewing. A thanks as well to those who have followed and favorited! Well, now that I've shared my two cents, better get on with what you came here to read, no?**

"_It's complicated. Charlie, could you get Balthazar to handle the wheel for a bit? I need to talk to Bobby."_

_The curiosity was blatant in the pirate's green eyes, but she nodded. "Aye, aye cappy," giving a fake salute she jumped down the staircase leading up to the wheel and searched out the active first mate._

_Once more Dean sighed and released the wheel after noticing his white knuckles. Descending the staircase, the pirate captain made for his chambers. He held onto the doorknob for a moment, realizing how long it's been since he was last inside. Slowly his hand turned the knob. _

* * *

Dean pushed the door open, taking a moment to look around at his redecorated room.

"Awesome," the pirate muttered as he looked at the various red and white banners that were scattered about his walls. One by one the captain ripped them from the walls, until he reached his desk with a fistful of wasted banners.

Upon his desk was a map, but Dean had no such use for this map. With a sweep of his hands he cleared his counter of assorted official documents. He watched as they flew and scattered about in the air before settling onto the floor.

Pleased now at the fresh look, the pirate captain tossed the banners on top of the fallen papers, watching as they slowly unraveled while remaining crumpled. Dean's fingers traced the edge of the desk as he walked behind it, pulling out the chair. All at once he slumped down into the old chair, appreciating that the navy hadn't messed with his father's furniture.

His eyes slid down the sides of his desk until they landed on a familiar set of scratches. Lightly his hand ran over the marks, rubbing his thumb over the carved letters that he recognized; sloppy as they were. He traced them with his finger, fluently following his familiar signature of D.W, but he froze when he moved onto the next set of initials. Subconsciously Dean began to chew the inside of his lip, his mind was at a standstill as was his hand.

"Dean?" An old gruff voice pulled the pirate captain out of his silence, jumping at the sound of Bobby's voice.

"Jesus Bobby, knock first before you want to give a man a heart attack." Dean joked, telling his heart to slow down while he drew his eyes away from their first target.

"You're the one that wanted to see _me_, idjit." Bobby's voice was Dean's anchor as he tried to shove away the boiling feelings inside of him right now. As Bobby closed the captain's door Dean walked over to the front of his desk, leaning back on it with arms crossed.

Bobby raised an eyebrow inquisitively as he approached the Winchester, stopping just short of the younger pirate before crossing his own arms.

"Are you waiting for an invitation, son?" Dean locked eyes with the older man, trying to figure out how he wanted to ask the father-figure. Finally the captain gave up, and instead spoke plainly.

"How come Cas recognized you, Bobby?"

* * *

Gabriel brushed his hands together, pulling Castiel out of his thoughts. The younger Novak brother watched as his brother sat up. Castiel slowly unravelled from his previous position, having drawn his knees to his chest and had his chin resting somewhat on his kneecaps. He looked at his older brother expectantly.

"Any ideas Cassie?" Castiel's gaze swept over the entirety of the room, eyes wide as he tried to notice every little crook and board.

"Possibly," the younger Novak replied, "how do you think Bobby knows of Dean Winchester?"

Gabriel grimaced, "I never really liked Singer." Castiel arched an eyebrow at his brother before smiling slightly.

"You only say that because he managed to catch you off guard." The older sibling muttered a retort, instead trying to bring back Castiel's attention.

"Focus Cassie, any way out?"

"Of course there's a way out Gabriel. But then what?"

"Improvisation," Gabriel suggested, and smirked as he watched Castiel shake his head, "would you rather stay here so you can talk to Captain Winchester, you flirt?"

Castiel narrowed his eyes at his brother, arms crossed now as he stood up. "Seriously, Gabriel? The man's a criminal and you want to talk about flirtation?"

"Just saying, I saw you two and you were definitely in the heat of the moment back there." Gabriel's smile remained as he watched his brother turned away with anger in his eyes, along with a flicker of something else.

"If I get us out, you think you can get us back to Darton?"

"Don't want to pursue your boy toy, Cassie?"

"Gabriel," Castiel warned, his voice low as he continued to look away from his brother.

"I think I could come up with something, I don't just stare at the sky in deep thought like you brother dear" Gabriel replied, shrugging his shoulders even though Castiel couldn't see. The younger sibling glanced back towards his brother before releasing a sigh.

Castiel approached the front of the cell, and turned to face Gabriel. His eyes locked onto the bench that his brother still sat on.

"Get up," Castiel ordered. Gabriel stared at Castiel curiously, wanting an explanation.

The former sailor pointed back to the door on the cell.

"Those are half-pin barrel hinges," Castiel's blue eyes flicked back towards the bench, "with the right kind of leverage and the proper application of strength, the door will lift free."

Gabriel's gold eyes filled with understanding and he immediately sat up from the bench. His eyes twinkled with pride as he looked at his brother. Together the two picked up the bench and Castiel commanded how the bench should be set. Two legs of the bench went through the gaps made by the crisscrossing bars, and with a cooperative effort the two shoved the bench down, and were met with a gratifying metal on metal sound as the door popped free.

"We better hurry, someone could've heard that." Castiel stepped out from the cell, casting his blue eyes around the room.

"Yeah of course," Gabriel began as he walked towards the door before turning around to face his younger brother.

"Hey Cassie, if you're so observant, why didn't you see how Winchester was going to get out?" Mischief danced in Gabriel's eyes as Castiel's eyes narrowed, although his younger brother's face turned red slightly.

"Bigger problems here, Gabriel."

* * *

Bobby was silent for a moment before walking over to a chair that sat against the left side of Dean's room. With a sigh Bobby sank into the chair, resting his elbows on the chairs arms while his hands settled on his stomach; fingers intertwined.

"Well like I said earlier, Castiel was a former sailor for the Royal Navy. I used to sail for the Navy too boy, if you can recall. Wasn't always assisting pirates and Lord knows what else I've done with you boys."

Dean's eyes were focused on Bobby, whose gaze was drifting between the captain's eyes and his own boots.

"Look kid, Castiel sailed under my command for a bit. He was a good kid, young and respectful. Nothing like either of his brothers; real quiet-like."

Dean nodded, his eyes distant as he thought about the former sailor.

"Definitely an oddball," the pirate captain muttered, and shook his head before making Bobby the focus of his attention once more.

"So, guess this is like the old times all over again; you back on the _Impala_."

Bobby smirked. "Sorry for the sudden intrusion kid, wasn't really my call either. Noticed those two running down the street and figured you could appreciate the help, savvy?"

"Aye, we're savvy," Dean replied, looking at Bobby. The man looked tired, as always, the way he sagged into the chair along with the darkness that collected under his eyes.

"Anyways, why don't you go rest up or something Bobby? You look like you've been avoiding sleep."

"I'm old boy, I'll sleep when I'm dead," Bobby countered as he stood up from his chair and began to head towards the door. Dean chuckled, but the feeling of concern lingered on the captain.

"Just take it easy, okay?" He watched as Bobby turned around to face the Winchester, a seriousness that wasn't present before came to his voice.

"Kid, I ain't the one who should be-" Dean intervened before Bobby could finish.

"I'm fine, Bobby. Okay? I'm fine. Go take a nap or something." Bobby stared at Dean silently, his eyes lingering on the pirate's green eyes; trying to convey all of his silent prayers and questions to the boy. Wordlessly the older man returned back towards the door and left, leaving Dean to his own.

The pirate captain stared at the door long after Bobby had left, his mind working through his scattered thoughts. Faintly he felt it stir, the dark spot in his head. With panic Dean jumped from inside his head and back out into reality.

Walking back over to his desk, the pirate captain slumped into his chair. Eyes were locked once more onto the carving on his father's desk, but he began to feel drained. After all of the day's excitement, Dean couldn't help but begin to close his eyes; his energy had been spent. Knowing that Balthazar should be able to get the others situated for now, the Winchester collapsed into an awaited slumber.

* * *

Cautiously Castiel walked ahead of his brother, wooden board in hand. The object was solid, and the Novak brother felt better having some sort of weapon. The stairs creaked slightly at the pressure that was put down on them by the Novaks' feet, and every time both brothers paused; waiting for someone to hear the now free siblings.

The two were surprised when they managed to get to the top of the stairs, and began to slowly embark down the long corridor that followed.

"You think they're all up top?" Castiel paused as he whispered to Gabriel, who shrugged before realizing his brother couldn't see him.

"Who knows, that would be something good for us for a change," Gabriel quietly replied, his eyes occasionally flicking up towards the sound of pirates walking on the deck. The younger Novak nodded, his eyes glancing up as well at the sound of footsteps above them.

Soon the two reached the end of the hallway, and a door stood before them. Gingerly, Castiel pressed his ear against the door, listening for anyone to be in the room. Quietly Castiel listened to the rhythmic snoring that came from the other side; he looked back towards his brother.

"There seems to be someone sleeping, other than that I assume everything else is coming from the actual deck above us."

"Assume?" Gabriel quizzed, eyebrow raised while his eyes flickered to the wooden boards above him.

"No one's perfect brother," Castiel snapped with a hushed, low voice. Gabriel shook his head, trying to hide his small smile from his younger sibling.

"Fine. Just continue; quietly would be favorable."

"I'm not a moron Gabriel." The younger Novak narrowed his eyes at his brother as the older sibling snorted. But they remained silent as they continued to hear the constant footsteps above them.

Gently Castiel rested his hand on the doorknob attached to the start of their way into the main room. Gradually he turned his hand at a painstakingly slow pace, both were silent as they subconsciously held their breath. The click as the doorknob reached the end of its rotation seemed to shout in the hushed air.

Castiel winced as he pushed forward on the door, and it responded with a faint creaking noise. He could almost see Gabriel's facial expressions as he proceeded to slowly open the door, his grip on both the doorknob and the board in his hand iron-tight.

Finally the doorway was wide enough, and Castiel cautiously peaked through the crack, his eyes scanning the empty room save for the sleeping man in a hammock. Recognition flashed in Castiel's eyes and he turned to alert his brother.

"It's Bobby," the younger Novak told his elder brother in a hushed voice, noticing the slight narrowing of eyes that Gabriel responded with. But it disappeared in a flash as Gabriel transitioned back into his usual smirk.

"Since when does Bobby Singer sleep? I thought that man was an insomniac." Castiel tilted his head in response before turning around to face the nearly empty, spacious room once more.

"Now is the time for silence, Gabriel." Pleased by the quiet that responded to Castiel, the younger sibling began to step out of the hallway and into the sleeping quarters. Striking blue eyes remained locked onto a sleeping Bobby as Castiel left the cover of the hallway and its doorframe.

Just as Gabriel began to follow, the two boys froze at the sound of laughter and approaching footsteps descending down the open stairwell.

**As always thank you for reading and I hope you enjoyed this chapter. I'm starting to form a schedule, I would probably post three times a week; as soon as I get it completely figured out I will let you all know! Please review, favorite, or follow if you enjoy this story! **


	8. Racing With Time

**Welcome back everybody! Here we are for another update of Pirates! Thanks to fictionfairytalesfantasy4921(and it seems your hopes shall be answered ^_^), DeerTopus C. VonZenHousen (your idea shall be considered!), mywarisalreadywon(glad you like it!), and Kather-Swine for your reviews. A thank you as well to those who have followed and favorited! Now let's continue, shall we?**

* * *

"_Now is the time for silence, Gabriel." Pleased by the quiet that responded to Castiel, the younger sibling began to step out of the hallway and into the sleeping quarters. Striking blue eyes remained locked onto a sleeping Bobby as Castiel left the cover of the hallway and its door frame._

_Just as Gabriel began to follow, the two boys froze at the sound of laughter and approaching footsteps descending down the open stairwell._

* * *

"Hide," Castiel hissed to his brother, whose eyes were trained on the stairwell and the beginnings of feet on descending steps.

The two frantically jumped for cover. Castiel chose to slip behind a set of barrels, leaping into the safety of their shadows and size. Desperately the older Novak looked for a safe spot, Castiel watching with pleading eyes as he glanced towards the nearing crowd of pirates. Cursing, the elder brother rushed back towards the hallway, slipping behind the door just as the group entered the main sleeping quarters.

"It's odd, being back and all. Good, but odd," a voice from the many stated, and there was murmur of agreement among the rest.

"Although I wonder where Dean was that whole time, you know? I'd trust the man with my life, but he just disappeared on us. That's not something you do to your family," quietly a different voice spoke, and once more there was another buzz of understanding, yet this time much quieter and serious. Castiel listened as the group remained silent, awkwardly standing among one another while he hid. An accented voice that made Castiel's eyes narrow called out to the others.

"Alright you filthy pirates, we know that Dean wouldn't leave like that without good reason. I'm sure he'll share when he's ready. But we all came here with the promise of not questioning and trusting the man like we have before, so lets stick to our side of the commitment, savvy?"

Balthazar smiled at the unanimous agreement he received from the others, "all right, now which one of you lucky ducks wants to sweep the ship before bedtime, eh?" The group grumbled while the first mate's eyes swept across the group, searching out for a volunteer. Castiel kept his head low as he watched with a slight curiosity, though he remained tense and ready; both hands clutching his wooden board.

"Ah, Garth. So lovely of you to offer up your kind services," Balthazar smiled at the thin man, who grumbled before taking the lantern out of the first mate's hand. Castiel ducked down as the pirate began to head towards the hallway that Gabriel headed in. A pit grew in his stomach, he couldn't let them catch Gabriel. Resolve filled within Castiel, and the former sailor acted in the defense and hope for his brother.

* * *

After Dean managed to fall asleep, his mind felt open as memories seemed to drift past him.

_A younger boy asking to get candy, eyes wide and innocent. Unable to resist, a young Dean Winchester led his brother inside the store; enjoying the look of happiness that danced in his brothers eyes._

_As Dean opened the door, he walked into another memory. This time he was on a ship, his ship_. _He noticed both his brother, older than before, along with a man he knew was his father. Together the three were standing back to back, fighting off enemies that the pirate captain didn't bother to identify. It was easy to recognize the feeling of love that was felt by the three._

_Suddenly Dean was looking at his brother once more, eyes determined as he turned around and walked away. Left behind was a distraught older brother, left alone now without a father or a brother to turn to, to count on. But he was soon embraced, and it was easy for the Winchester to recognize his crew before him. They stood by his side, loyal and understanding; family._

_But once more Dean stood on the Impala, he looked around to try and recognize where they were. Silence filled the night saving for the lapping of water on land, and Dean stared at the island that his boat was on, along with another ship that remained beached near his own._

"_It's time to go, Dean Winchester," a voice called from behind him. Panic rose in Dean, recognition slamming into him and his conscious._

"No!" Dean shouted as he awoke, his heart pounding while he sat up in his chair. Eyes wide, the pirate captain tried to relax, breathing deeply. Once his heartbeat slowed, the Winchester rubbed his eyes before turning his chair around to look through the window in the back.

Still dark, Dean was silent as he looked at the dark ocean with it's starry counterpart. He took a moment to admire the reflection of the stars, which flowed and moved with the waves.

Closing his eyes, the captain rested his head against the window as he leaned forward. The sounds of the ocean was peaceful, and Dean appreciated his and his father's career choice. His mind began to drift to his father, until it began to poke and prod at the steel box that was settled in Dean's conscious.

"No," he growled at himself, turning back towards the desk. His eyes were drawn to the familiar scratch marks that he had already found himself staring at constantly, but he forced himself to look away.

Angrily Dean faced the calming ocean to try and calm down. Noticing his reflection in the window, the pirate stared at his image. His face was haggard, the way his eyelids drooped slightly along with the dullness of the spirit in his eyes. Dean Winchester was an infamous pirate, but this didn't make the man a god. Even mortals like himself needed rest, but that was the last thing he wanted; to return to the nightmares.

He closed his eyes, taking a deep breath again to pacify the swelling anger inside of him. Dean did not want to feel the rage, the anger that was stabbing him, wanting to be noticed and satisfied.

However, Dean was drawn out of the quarrel inside of him as he heard a commotion going on below him.

"What the hell are those maniacs up to now?" The captain muttered before heading towards his door to see just what his crew was up to at such a late hour.

* * *

Castiel launched the barrels at the pirates, one at the group before throwing one at Garth. Hurriedly he rushed through them, heading towards another hallway opposite to the one his brother hid in.

He cast a glance, and through the crowd he could've sworn he saw a glimpse of his brother's eyes before he threw the door open and entered the hallway. Quickly the former sailor locked the door, and he jumped as it was pounded on the other side, the knob refusing to turn all the way. Smiling slightly, Castiel turned and began to rush through the hallway, looking for somewhere to hide; to stall for the sake of his brother.

Deciding to head down the stairs, the younger Novak brother thrust the door at the bottom open, revealing a supply room. His heartbeat was loud in his ears as he heard the previously locked door get forced open.

"Search all the rooms!" An accented voice commanded, and he listened as doors began to open above him. Eyes scanning the room, the former sailor searched for a proper hiding spot.

Time, that was all he needed to give to his brother. Gabriel was smart, kidding around put aside, and could easily find his way back to Darton and know where the _Impala _currently was located. So Castiel would provide time, it was the only option he had left.

Deciding to make the supply room his last stand, Castiel gave up on the hiding spot and locked the door. With speed the former sailor began to barricade the door, shoving as many heavy items in front of the door as possible. It wouldn't keep them out, but it would take them time.

And that's what Castiel needed to provide.

* * *

Gabriel watched with surprise as his younger brother jumped from his hiding spot, throwing barrels at the pirates with accuracy. Catching them off guard, his brother raced to the other side of the room, and for a moment their eyes locked. The older sibling could've sworn he saw the small smile his brother gave him, the confidence and determination in his eyes met with Gabriel's surprise and understanding of the message relayed through their shared look.

_Get out._

Quietly Gabriel smiled slightly as the pirates took the bait, attacking the door that his brother had locked. Finally the door gave way, and the crew filled the hallway, none of them noticing as the older Novak quickly snaked his way through the doorway and up the stairs to the deck.

As he reached the top of the deck, Gabriel took a moment to look at the stars, trying to figure out where he was and how far away he was from Darton. But he was interrupted as he heard a door begin to open ahead of him.

Heart racing, Gabriel dove to his right, managing to reach the edge of the cabin before bringing himself behind a tarp holding down a stack of barrels. With silence the elder brother watched as Captain Dean Winchester began to walk towards the staircase Gabriel had previously been near. The captain's eyes glanced around the deck of the ship as he descended, not noticing the hidden Novak brother.

Once the pirate captain had reached the bottom of the stairs, Gabriel rushed from his hiding place and to the object of his desire. He ripped the tarp off of the lifeboat that rested near the edge of the boat.

After a bit of work, Gabriel managed to get the boat off the deck and over the edge of the ship. Glancing towards the stairs, the elder brother could only imagine what Castiel was doing to give him time, by the sound of it they had yet to catch him; Gabriel smiled slightly at the thought.

Jumping into the lifeboat, the royal officer began to lower himself from the _Impala_'s side; focusing on not dropping himself. But his arms began to scream at his slow descent, the weight he had to hold was beginning to become unbearable. Glancing down to the nearing water, Gabriel gritted his teeth.

"Screw it," he muttered as he released the ropes, and all at once he and the boat fell before reaching the water's dark surface. Jarred after the landing, Gabriel took a moment to collect himself, making sure the lifeboat was fine before glancing at the _Impala_. Sitting down and picking up the paddles, Gabriel began to row. His eyes were locked onto the mighty ship until he finally turned around and directed his attention to the stars. A thought burrowed itself in his head, playing on loop as the distance grew between him and the dark ship.

_I'll be back for you, Cassie._

* * *

Castiel sat down on a stool far away from the door, listening to the continuous pounding on the door that had started only moments after he barricaded it. Smiling slightly at his work, the former sailor continued to hear the curses and onslaught. Until a commanding voice spoke up among the others.

"What's going on here?" He tensed at the sound of Dean Winchester's voice, hand clenching his wooden board tightly. Blue eyes were locked onto the door as he listened in on the conversation.

"Man somehow managed to get out of the brig. He was hiding behind some barrels before he threw them and darted into here. I'm assuming he locked and barricaded the door the _twit!"_ Castiel recognized the accented voice of Balthazar's, and his grin returned at the sound of the man's annoyance.

"What about the older guy?" The former sailor heard the captain ask, and his heartbeat began to increase. Although he couldn't help but enjoy the turmoil he had created, Castiel was terrified that he couldn't get his brother what he needed, the time he had tried to provide.

"We don't know whether or not guy's in there or if he's somewhere else." Sighing Castiel closed his eyes.

_They haven't found him yet, he could be off the ship by now. _The thought comforted the younger brother as he awaited his inevitable recapture.

"Garth, Charlie, and Jim. Go check the rest of the ship, make sure that he's either not there or he's in here." Castiel listened as the captain commanded his crew.

"And hurry up and open this door!" A smile grew on his face at the sound of the captain's annoyance as well. Once more the pounding on the door began, settling into a rhythmic, harsh noise.

Finally he heard the door's lock give, and the crew along with its captain began to push the door open; trying to get past all of the weight on the other side. At first it was just a crack, but gradually they managed to open it wider and wider. Castiel had watched, half of him calm while the other half was worried for his brother. His ears perked though at the sound of emergency in one of the pirate's voice.

"Captain! One of our lifeboats is missing from the deck!" Castiel smiled, shaking his head as he looked up to the wooden boards above him. His brother had made it out, he had provided enough time for him.

After hearing the news of his brother, Castiel released the wooden board he had held in his hand, resting it on the table beside him. He counted how long it took for the pirates to work on the door, the process relaxing his heart as he embraced the fact that he had succeeded in what he had intended. Gabriel was free.

At last the pirates with their captain had shoved the door open, and they flew into the room; swords and pistols drawn. Soon their attention and weaponry was focused on the former sailor, who sat quietly on his stool. They remained silent as a man with forest green eyes walked up to Castiel, stopping just short of the younger Novak brother. Castiel watched as the captain's eyes searched his own, their eyes locked in the eerie silence. Finally Dean spoke up, their eyes still focused on each others.

"Where did he go?" The captain asked, his voice strong and authoritative. Castiel raised his head up slightly, tone deep and confident as he replied.

"I think we both know where Gabriel is headed."

Dean pursed his lips as he thought about Castiel's reply, but he nodded. Without turning to the crew, the pirate captain's eyes remained trained on Castiel's.

"Balthazar, bind his hands than bring him to my quarters. I need to talk privately to Cas here." Turning around, the captain began to make his way back towards the door. But Castiel decided to ask what had been on his mind since the first moment he had met Dean Winchester.

"Why the hell don't you just _kill_ me?" He shouted irritably at the pirate, who froze slightly in the doorway at the former sailor's outburst. The pirate crew was silent as their eyes were focused on Castiel and their captain. They watched as his head turned, the two staring each other down in a death-like quiet before Dean smirked.

"Like I said Cas, I don't make it a habit to kill pretty boy swordsmen." The pirate captain knocked on the wall before exiting the room, leaving a victorious crew and a confused Castiel to his own thoughts.

**Whew! I believe this is my longest chapter so far, and I hope you enjoyed it! Hope you have a good day, and please review, follow or favorite if you want to. See you for the next installment ;)**


	9. Damn Curiosity

**Wow, seems the previous chapter was well received! Thanks to Air Guitar Pixie(it's perfectly fine, no need for apologies! thank you so much, I'm honored that you love the story so much! ^_^), Deer Topus C. VonZenHousen(your version isn't quite what I'm shooting for ;), The Mysterious Shadow and mywarisalreadywon( never fear, a new chapter is always around the corner!). Thank you guys so much! A thanks as well to those who follow and favorite. I've never written a story this long, and I have big plans for it! Well, back to the story, shall we?**

_Turning around, the captain began to make his way back towards the door. But Castiel decided to ask what had been on his mind since the first moment he had met Dean Winchester._

"_Why the hell don't you just kill me?" He shouted irritatedly at the pirate, who froze slightly in the doorway at the former sailor's outburst. His head turned, and once more their eyes locked before Dean smirked._

"_Like I said Cas, I don't make it a habit to kill pretty boy swordsmen." The pirate captain knocked on the wall before exiting the room, leaving a victorious crew and a confused Castiel to his own thoughts._

* * *

Castiel was silent as he watched the rest of the pirates leave the supply room, leaving only him and Balthazar. The pirate kept a wary eye on the former sailor while looking for rope. But Castiel remained where he sat, watching quietly as Balthazar found the object of his desire and walked towards the younger Novak.

"So I'm assuming this was all for your friend of yours to escape?" The first mate asked when he approached Castiel.

"Older brother," Castiel corrected with a whisper, his eyes drilling into the floor while his thoughts were trying to organize themselves from the chaos that was going on inside of him.

"How sweet. Now could I see your wrists?" Balthazar's voice was surprisingly soft, and it pulled Castiel out of his mind, his eyes darting up to look at the pirate's. The former sailor brought his arms together, and Balthazar began to work.

"You know," the pirate started while wrapping the rope around Castiel's wrists, "for a man who has tried to escape twice, you're being awfully submissive." Once again Castiel was surprised by the softness of the pirate's voice.

"He needed time and I provided. I chose the course of action, and he got out." Castiel replied, his blue eyes distant even though they were staring at Balthazar's own.

"That he did. Come on now, best we be on our way. You've certainly made this an interesting reunion for our first day back on the ship," Balthazar spoke as he led Castiel, resting a hand on his shoulder while keeping another on his arm.

"But that's just the thing, isn't it? I'm currently on a ship filled with pirates about to do Lord knows what. Tell me, if I have been such an annoyance in your attempts on sailing away, why am I alive? Answer me that, Balthazar." Castiel stopped, his eyes locked onto Balthazar's; who hesitated at the sight of Castiel's eyes. They burned with anger, but behind the burning look was something else, exhaustion or confusion; Balthazar wasn't quite sure.

"Look Castiel, in our line of work most would kill you on the spot. But," Castiel watched as Balthazar searched for an explanation, before giving a sigh of resignation. "It's complicated."

Castiel snorted, looking away from the pirate and allowing his gaze to drift around the hallway.

"You're not going to try and hit me again, are you?" Balthazar joked, Castiel squinted at the older man as his statement caused him to be the former sailor's attention once more.

"You're strange, Balthazar." Curiously Castiel watched as the pirate chuckled before beginning to lead the younger Novak brother through the hallway again.

"Yeah, I get that a lot. But that's what makes me so charming," Balthazar responded with a dazzling smile. Castiel continued to gaze at the pirate with a confused look. In turn Balthazar shook his head, a smile still on his face.

They reached the staircase leading up to the deck, and Castiel looked up to see a still night sky, the stars were more clear and noticeable compared to the last time he looked.

Together they slowly walked up the stairs, Castiel's eyes still on the sky while Balthazar glanced at the former sailor occasionally. Once they reached the deck, Castiel looked at the ship's surroundings; hoping for a possible landmark. Alas, the only thing around the _Impala_ was the dark ocean, waves lapping against the boat as it continued to sail across the water.

Pulling Castiel along, Balthazar led the younger man over to the door of Dean's room. The former sailor cast one more longing glance at the sky and its stars, trying to find a pattern before Balthazar yanked him from the doorway and into the pirate's quarters.

* * *

Dean sat down in his chair, resting his elbow on the arm of the chair before leaning his head against the raised hand. He turned his chair, staring out into the mysterious ocean as he had been only moments before. Releasing a sigh, the pirate began to close his eyes. Hard as he had tried to avoid sleep, but he knew it would be inevitable. His body still ached from his short-lived flight, and the day had seemed to never end; compliments of a certain rebellious Novak.

The pretty boy swordsman seemed to call out to Dean, he couldn't help but be curious about the man. Especially the way he seemed to be wherever Dean went. Hell, just his eyes seemed to disturb the Winchester. It was as if Castiel could stare into your soul, see everything with just a glance.

Sure it would be easy to just kill the mysterious man, but it wasn't in Dean. He's been around enough death, enough for a lifetime. Shuddering inwardly, the captain's eyes opened to try and avoid the inevitable for just a while longer. A problem still had to be resolved.

What to do about Castiel Novak?

The opening of his door drew Dean out of his thoughts, knowing who was going to be on the other side of that room. He smiled at the sound of Balthazar giving a huff as his first mate must've pulled the former sailor into the Winchester's quarters.

"Delivery, Oh Great One," Balthazar called out, and Dean's grin grew before he sobered up, still facing the window in his chair.

"Thanks Balthazar. Are we still on course?"

"Aye, she's making great time." Dean nodded, and listened as a single pair of footsteps walked back towards the door, it closing with a soft click. Silence gathered as the captain closed his eyes, taking a deep breath. Knowing who was on the other side of the room was one thing, confronting the person was a whole other obstacle.

Standing up, Dean kept his eyes on the window, trying to figure out what he wanted to know. The he turned to face his adversary, the man in the familiar tan coat with the striking blue eyes.

"Hi again Cas," Dean started, keeping a mask over his head by withholding a smile from entering his face. Castiel was quiet for a moment before he spoke up with his surprisingly low voice.

"Hello Dean," The pirate admired the fire that seemed to still be in Castiel's eyes. Even though the man was a prisoner, had failed to escape twice, and had lost to Dean twice now the determination and anger was bright in his eyes; although this poked Dean's curiosity.

"Your eyes are unusually bright," he accidentally blurted out, and the captain felt his cheeks glow red. Although he wanted to smirk as the captive shuffled his feet a few steps back, immediately bringing his face down. Dean could only assume that Castiel as well was trying to hide the red of his own face from embarrassment; the pirate tried to amend the statement.

"What I meant," the pirate captain began to collect himself, "was that for a man who seemed to want to die earlier your eyes are screaming determination and anger."

"I wasn't trying to get myself killed," Castiel muttered loud enough for Dean to hear, "your pirates. The last thing one expects is for you to keep prisoners." The younger Novak lifted his bound wrists for emphasis, the color from Dean's previous remark fading away from his face.

"Does that make me special?" A familiar smirk came across the captain's face as the two stared each other down.

"It makes you different."

* * *

Castiel meant every word that he said to Dean Winchester. From the moment he had met the pirate, he knew that Dean was different from the usual. The way he talked, it was as if the pirate was always trying to hide behind a wall of bad humor. Hiding, Castiel was positive that that was what Dean was doing. And, against his better judgment, it drew in the former sailor's curiosity.

The smug look remained on the captain's face after Castiel made his reply. "Well aren't you a flirt," Dean's eyes confused Castiel, the way they had a joking light mixed with something, well _dangerous_ was the glint that he saw in the pirate's eyes.

The former sailor's eyebrows drew together as he looked at Dean with confusion, his head forming its usual angle. "I'm hoping that the reason you wanted to talk to me was more than the idea of flirtation," Castiel tried to break down the pirate's behavior; Dean Winchester was certainly different. Though the former sailor decided to use the term 'different' loosely.

The captain scoffed, his green eyes still alight, almost twinkling like the now present stars. "Me, flirting? You certainly are strange pretty boy." Castiel's eyes narrowed at the sound of the pirate's strange nickname for him, though he remained quiet.

Dean smirked at the former sailor before his face grew serious. The pirate walked over to his side of the desk, Castiel noticed how Dean's eyes seemed to focus on something near the bottom of it.

"What do you of the _Hellhound_, Castiel?" The younger Novak brother was surprised by the captain's use of his full name, but he maintained his usual expression as he found himself walking away from the door and towards the pirate.

"Do you mean that ship they used in children's stories?" The former sailor took a moment to search his mind, keeping his eyes locked onto Dean's; although the pirate kept his face looking down at his desk. Once more the Winchester drove Castiel crazy, why was this pirate so interested about a children's tale? "It was a ship claimed to be sailed by the devil himself, right? He would trick people, commit terrible deeds."

Castiel awaited to see a response of any kind from Dean. Finally the pirate looked up, forcing himself to meet Cas's curious blue eyes. The former sailor then noticed how tight Dean's grip on his desk was. His whole body seemed rigid. But as soon as the captain met Castiel's eyes, he seemed to loosen a bit.

Damn Dean Winchester for making Castiel so damn curious about him.

Silence was the only form of conversation between the two, finding themselves staring into each others eyes as one awaited the other. Clearing his throat, the captain straightened up while he maintained eye contact with Castiel.

"What if I were to tell you that the _Hellhound_ was real, Cas?" Immediately Castiel snorted, but the look in Dean's eyes made him pause. Green eyes that were serious to the pupil, spots of anger while altogether trying to shield out something else, something Castiel couldn't make out.

"You're not serious?" But the look in the captain's eyes was all the confirmation that the former sailor needed and received from Dean. Although his mind filled with questions, he asked the one that seemed to scream the loudest.

"Why tell me this?"

* * *

Dean also asked himself this deep down as Castiel inquired why Dean was sharing this information. Why should he even bother to talk to the Novak? He should just find some island and dump the man there, simple and easy. But the Winchester understood why he wanted to tell Castiel, now that he knew that he was in the dark. He cursed at himself in the inside.

Damn Castiel Novak for being so, well damn him for being Castiel Novak!

The words began to form in his mouth, but he couldn't find himself able to share the news. So he decided to come up with a reasonable answer as the former sailor stared him down.

"Understanding." Mentally Dean was shaking his head, but at least he could give a slightly honest answer with his excuse.

"Understanding," Castiel repeated, and Dean knew that the former sailor didn't buy it. Silence began to flood the room again, and the captain tried to think. Not only did he still not know what to do about his 'prisoner', he wasn't still too pleased about the other one escaping. Deciding to start a list, Dean began his interrogation.

"Did you know the other guy that escaped?" He admired the slight lift of Castiel's chin in defiance as the former sailor's eyes burned with pride.

"His name's Gabriel, and yes I know him." Dean nodded, to be honest he knew he could get over the escapee, so he continued.

"How'd you get out of the cell?" The pirate was especially curious as to how Castiel would answer this. Once more their almost seemed to be an air of pride that surrounded the former sailor as he replied.

"You should update your security, I expected better."

"Says the man who stayed behind." Dean's eyes narrowed slightly, he didn't like how the Novak was acting so arrogant.

"And got the other one out," Castiel countered, his eyes also narrowing.

"If you're not on my level, then how come in just one day I have managed to beat your ass against your attempts at capturing me?" A smirk blossomed on Dean's face after his own counter to Castiel's. The former sailor's eyes narrowed even further, his eyebrows knitted together.

"You cheated the first time." The pirate captain couldn't help but give a short laugh, his previous growing anger melting away. Holding himself back, Dean kept from laughing again after noticing that Castiel remained angered; although his eyes were twinkling with their own laughter.

"I'm serious," the former sailor argued, "it is not fair to pull a firearm during a sword fight." Once more Dean burst into laughter, and this time he found himself hugging his sides. His eyes met with a pair of blue eyes that were completely annoyed, but still the captain laughed until he managed to calm down.

"Sorry, but you sounded very child-like just then," Castiel was about to argue but Dean continued before he could interrupt "I haven't seen such a serious face over such a thing like that since Sa-"

* * *

**Don't you just love cliffhangers? Why the sudden change of attitude from Cas, and what's in Dean's past that has scarred him so much? I love leaving you guys to ponder these things ;) Happy Fourth of July to all you patriotic Americans, and have a wonderful day for the rest of you! Please review, follow, or favorite if you enjoyed!**


	10. Losing Streak

**And we are back! Hope you all are having a good weekend, mine's been swell. Thank you to Akayuki Sawada, Air Guitar Pixie (do you always stay up that late? As for your theory….), Dancerline (glad it didn't though!), Kather-Swine( that's the pain of a reader, not knowing!), Deer Topus C. VonZenHousen( I do know about the badassery that was Anna Bonny, and of course I wouldn't take it the wrong way), fictionfairytalesfantasy4921( all these theories about Sammy, you all must truly miss the moose huh?), mywarisalreadywon(do not fret, we have not seen the last of our sweet-loving big brother), and The Mysterious Shadow(thank you!). Now, let us resolve that nasty little cliffhanger I left you guys ;)**

* * *

"_I'm serious," the former sailor argued, "it is not fair to pull a firearm during a sword fight." Once more Dean burst into laughter, and this time he found himself hugging his sides. His eyes met with a pair of blue eyes that were completely annoyed, but still the captain laughed until he managed to calm down._

"_Sorry, but you sounded very child-like just then," Castiel was about to argue but Dean continued before he could interrupt "I haven't seen such a serious face over such a thing like that since Sa-"_

* * *

Castiel watched as Dean Winchester froze, leaving the last of his sentence open. The pirate was silent, dropping his head down and looking at the desk with a sudden interest.

Privately the young Novak began to tear at the new information. At first he had tried to anger Dean, wanting to get a reaction out of him, let him slip up through his emotions and reveal something-anything to him. Of course Castiel had been surprised that instead of angering the pirate he had caused him to laugh.

Castiel had almost enjoyed hearing Dean's laughter, it was loud and full. A kind of laugh that he would expect Dean Winchester to only use when he wasn't hiding behind his constant jokes and sarcasm. And laughter was the key apparently, unlocking the door and allowing the former sailor to catch a glimpse into whatever Dean was hiding.

Quickly he was drawn out of his thoughts as he noticed that Dean had been looking at him as his mind tried to organize itself. Castiel almost felt embarrassed to be caught staring off as he was thinking, but he was able to keep the color from rushing to his face.

Remaining calm, Castiel raised an eyebrow at the pirate, trying to signal as to why he had stopped mid-sentence. He frowned slightly as he saw the guarded look back in Dean's eyes, surprised to find that he missed the honest laughter that had been residing in them moments before. The pirate cleared his throat, eyes glancing back down at the desk.

"Nevermind. Look, Cas, I don't know what to do about you. Gabriel getting out is one thing…" Castiel watched as the Winchester didn't complete his sentence, and Castiel knew that so many possibilities could have finished that statement.

"And you don't want to kill me," the former sailor added, another curious thread that Castiel desperately wanted to unravel. Green eyes met with his own, and he noticed how Dean's lip tugged upwards, wanting to smirk like he always seemed to do. But the pirate resisted and nodded.

Weariness began to spread across Dean's face, and Castiel just noticed how tired his own body was. It seemed like months had passed since he had first caught sight of Dean, and yet that was only just this afternoon. The pirate seemed to read what Castiel was thinking, and he smiled slightly.

"Long day," the infamous captain remarked, and the former sailor was about to nod in agreement when he caught himself. This man was Dean Winchester, infamous pirate captain, not an ally! This was no time for camaraderie, especially with the enemy!

But Castiel's own eyes remained on Dean's tired green eyes. He noted how the captain's eyelids were drooping a bit, although Dean seemed to be fighting to keep them as open as possible. He sighed, shaking his head and closing his eyes. Half of him wanted to scream, to drag Dean's ass back into Darton's prison and drop him into the darkest pits available. The other half wanted to continue to talk to him and find out all of his secrets, to see what exactly Dean Winchester was hiding. Taking a deep breath, he cracked open his eyelids and immediately his eyes landed on Dean's. He tried to throw fire into both his look and his words.

"I'm not going to stay here forever, Dean. Try as you might I will get out eventually, and I don't plan on staying in the supply room next time." Although his face was serious, he almost wanted to smile at his challenge. Dean even smiled slightly, despite his growing weariness that was becoming more obvious by the second.

"Go ahead and try," the Winchester responded.

That was it, all that needed to be said about it between them. A challenge had been issued and accepted. In a sense it was almost like a game, and the two players were both confident on their chances.

* * *

Wordlessly Dean walked out from behind his desk and walked up to Castiel. He didn't grab a hold of his arm, no threatening look in his eyes as he stepped up to the former sailor.

"I'll walk you back," Dean explained and he observed how Castiel remained silent. Vibrant blue eyes still burning to the captain's surprise, the former sailor simply nodded and the look in his eyes dulled. Replacing the fire was exhaustion, although the previous flames that had controlled his gaze flickered behind the fatigue; the flames seemed to be immortal.

Together the two headed towards the door, Dean walking slightly ahead of Castiel until they reached the door. Winchester's hand rested on the knob before he twisted it and held it open. Jokingly the pirate even took off his hat and held it against his head.

"After you, good sir," Dean offered, a smile plastered onto his face. Weariness was met with light in the pirate's eyes. Castiel paused, staring at Dean with his typical look before slowly walking out the door. Rolling his eyes, the captain placed his hat back on his head and closed the door.

Walking behind Castiel, Dean noted how the former sailor's head was tilted up, taking slow steps. It was easy for the captain to figure out that Castiel was staring at the stars, and taking his sweet time also. Reaching the stairs, he watched how the former sailor took one last longing glance at the night sky before he made his descent; Dean following.

As they reached the bottom, Dean glanced around the room. He smiled slightly at the sight of a slumbering Bobby, along with a few others that slept scattered about the room.

With hushed steps the captain led Castiel around his crew and down the hallway. Pulling a key from his pocket, Dean unlocked the cell next to Castiel's previous one, and opened the door for the former sailor. Wordlessly Castiel walked into it, Dean watching as the former sailor's eyes raced around the whole room. A smile began to grow on the pirate's face at the sight of blue eyes constantly moving, but he managed to cover it before closing the door.

An old song began to stir inside of him, and Dean began to whistle as he walked away from an observant Castiel. As the pirate walked up the stairs, he decided to say farewell to the former sailor.

"See ya, Cas," Dean called, his boots hitting the wooden boards that formed stairs as he casually walked up. Pausing slightly, the pirate waited to see if Castiel would answer. After silence began to gather, Dean smirked and shrugged his shoulders before picking up where he had dropped the tune. The lyrics whispering quietly in his head as he carried out the anthem.

_The sea, she provides the man's greatest desire._

_If he so loves the sea as she do he._

_The sea, she will care, she will cry and she will fall and rise._

_But she will provide for those she loves_

_Sailors, serve the sea. And so does, the sea reward thee._

_Oh the sea provides_

* * *

Ten days. For ten days Castiel and Dean were constantly playing their game. Neither of them had forgotten the challenge that both had written. Castiel had promised that he would get off the boat, and Dean simply made countermeasures to provide a challenge. Ever since their late night chat, the former sailor would find a way to slip out of his cell. And every time, there would be only one obstacle that stood in Castiel's way. The rather obnoxious captain that was Dean Winchester.

It seemed that no matter how different Castiel tried to make his way off of the ship, that blasted pirate was always there to stop him. Even when he could sense that victory was near, a tall black boot would squash it like the small chance it had been. The crew even started keeping tally, which only frustrated Castiel further.

The lousy hooligans knew that by Castiel's fifth attempt that Dean Winchester was only toying with the former sailor, they knew that their captain couldn't be beaten. The confidence and trust in their leader drove Castiel mad; how could that man gain so much from his crew?

On the tenth night, Castiel stood on the deck with a stranger's blade in his hand. And across from him, with the ever-present smirk, stood his most frustrating adversary. With narrowed eyes the former sailor watched as the pirate captain began to take a step to his left, the well-crafted blade resting in the grip of his right hand. Soon the two were circling each other, Castiel's eyes burning with annoyance and determination while Dean's were filled with nothing but confidence and mischief.

"How'd you get out this time?" the pirate asked casually, his shoulders relaxed compared to Castiel's tense ones.

"Balthazar left the bench in this time. Required a little bit more muscle, but it was the same as the first time; rather easy." Castiel almost felt nostalgic at the mention of the first time he had broken out of the brig with Gabriel. He felt one of his heartstrings twinge, there had yet to be any sign of his elder brother or the Royal Navy. So Castiel relied on himself to get out, he wasn't going to be stuck on this ship forever. At least that was the idea, but considering his predicament being stuck on a ship commanded by Dean Winchester, it sounded a lot better in his head.

"Well that takes me back," Dean replied before lashing forward with his sword. Castiel easily deflected the shot, responding with an offensive maneuver of his own.

"You know, back then I actually thought you were a fearsome pirate," Castiel began as he continued to swing at the pirate, "but you're just a man with a strange humour." Dean feigned a look of hurt before turning onto the offensive, the two of them waltzing on the deck. The two's blades swung against each other, bringing each other closer. Castiel observed as his look of hurt changed to one of confidence.

"There ain't no other men like me," the pirate countered as he shoved Castiel away. Taking a moment, the two stood away from each other. Both tense and waiting for one to strike first, Castiel tried to collect himself as he breathed heavily. Another smirk appeared on Dean's face.

"Already tired?" The pirate wiggled his eyebrows at the former sailor, and Castiel could feel the hold on the rage that had been building up for the past ten days inside of him break. Anger overtook him as he charged towards Dean.

"You're such an ass!" Castiel snarled as he continued to lash out angrily at the pirate. Blow after blow he tried to land on Dean, who still maintained a face full of mischief and smiling at Cas. The younger Novak's eyes were filled with nothing but irritation, the urge to hit the Winchester motivating him. Yet Dean still blocked shot after shot that Castiel made to try and land a blow on him.

"Come on pretty boy, you need to try harder!" Dean teased, and Castiel seemed to quiver with anger as the pirate's eyes twinkled as if there were stars in them. Castiel paused, grabbing a fistful of hair on his head with his left hand.

"Aaahh!" He shouted as he sped up his pace, going faster and faster with his strikes. Feelings of excitement soon overwhelmed Castiel as he noticed how the mischievous look in Dean's eyes faltered. Yet the pirate's face soon grew serious, and they were soon both lashing and blocking each other's blows with incredible speed.

Castiel's heartbeat began to race faster as Dean began to push the former sailor back from his gain on the pirate, causing him to take a couple of steps back. Confidence began to fill the captain's eyes, and he pushed Castiel back, further and further until they were near the steps that led up to the wheel of the ship.

The two crossed swords, Castiel's glaring at the now confident pirate, but he was too slow to avoid the boot-covered foot that swung towards him. Landing on his abdomen, the former sailor was thrown back into the steps, his head hitting one of the many steps that he lay across.

Trying to recover the air that had left him, Castiel coughed and struggled to sit up. But a blade that was not his own stopped him from rising, leaving him to rest on his elbows. Dean kept his eyes locked on Castiel's as he bent down and pulled the sword out of the former sailor's hands.

"This is Balthazar's too, isn't it?" Dean asked while examining the blade. Castiel began to stand up, Dean's attention focusing back on the former sailor as he raised his sword; keeping it level with Castiel's chest. He eyed the sword that Dean continued to point at his chest, but there wasn't any threat in it.

"You know there's no need to point that thing at me you ass. We both know you aren't going to kill me," the small smirk on Dean's face confirmed Castiel's notion. Slowly the pirate let the sword hang on his side, both swords now in his hands. He didn't sheath either, they were there as a warning for the former sailor.

"It's too bad that you're still on a losing streak," Dean jabbed, his face victorious and cocky. Castiel clenched a fist, but he held back a vicious retort. Instead he looked up at the sky, releasing a large breath as he examined the stars. Bringing his attention back to the captain, Castiel noticed how the pirate was in a relaxed position once more.

"Where are you headed, Dean?" the former sailor asked as he cast his eyes about the ship and surrounding water she sailed on. It seemed that darkness was the only time of day that Castiel got to see above deck, beforehand he always had to figure out a new way to free himself; but slowly his ways out were diminishing. It was thanks to lady fortune for him to get out this night due to the first mate's mistake.

A wolfish grin appeared on Dean's face, and Castiel once more felt the urge to hit the pirate; but he resisted as he glanced at the two swords still being held onto by the captain. Sure, the pirate wouldn't kill him, but he said nothing about severely injure.

"I've got to make a stop, got to see a man about a horse," the pirate alluded, leaving his answer open to hundreds of possibilities. Frustration building up inside of Castiel again, the former sailor's eyes narrowed at Dean. But cracks quickly raced through the frustration, and Castiel's heart sank into defeat. He was just so tired, tired of trying to be a free man repeatedly only to have his efforts wasted because of the infamous pirate before him.

* * *

"Just let me go," Dean was surprised at the pleading in Castiel's voice, he'd never heard such defeat in the man's voice before. "Just let me go," the former sailor repeated before sinking down onto the steps that he stood on. Dean watched as Castiel rubbed his hands against his face, and he could see that he was trying not to cry.

His heart faltered, his previous mood being washed away by distress and confusion at the sight. Green eyes remained on a broken man who refused to look at only the edge of his coat. Dean's heart was split as he watched Castiel twist and play with his tan coat.

Before he knew Dean was sitting next to Castiel, swords left where he had previously stood. Running a hand through his hair Dean cursed, unable to decide what to do or say.

"Cas," he began as he looked at the fallen face that had settled on the other man, "Look man, I understand. It sucks, you were pulled away from those you know and love and you're stuck on a ship with people you never wanted to be with. I'm not gonna say it gets better, and I just don't know if I can promise you anything."

The pirate felt his stomach twist into several knots, he wasn't used to this type of conversation. Closing his eyes, Dean took a deep breath and became silent. The sounds of the ocean were soothing, the way they lapped at the boat's frame and rocked the mighty vessel ever so slightly. Never had Dean felt so at home than when he was here on the _Impala_.

Absorbed with the sounds of the ocean and his ship, it took Dean a moment before he heard something else that caused him to open his eyes. Slowly, the pirate turned his head to look at Castiel.

"Son of a bitch," Dean whispered with wide eyes at the sound of the former sailor snoring softly, his hair covering his closed eyes while his chin was tucked into his chest. Unable to stop himself, Dean chuckled quietly, trying to hold in his usual loud laughter.

And for a while Dean allowed it to remain that way. A beautiful night sky rested above them while the ocean and the _Impala _sang together; joined with Castiel's snoring.

A warm feeling began to blossom in the pirate's stomach. It was a feeling that he couldn't quite identify, but he didn't mind. It was a nice feeling, after all. Casting another glance at Castiel, Dean smiled a bit to himself.

Never had Dean felt so at home in a long time.

* * *

**Awwww, isn't that adorable? Thank you all for reading! Follow, favorite or drop a review if you want to! Have a lovely day everyone, thanks again!**


	11. A Captain's Authority

**And here we are for the next chapter! A thanks to Kather-Swine(not quite, sorry! I did consider doing that, but I decided to take a different approach) mywarisalreadywon( Aww thank you! I really appreciate hearing that, and I'll do my best to live up to that!) DeerTopus C. VonZenHousen (don't worry, I've got it all planned out, I've done my best to incorporate it. Although it may not be here for a bit, that doesn't mean they won't be here at all!) and Air Guitar Pixie( Virtual hug for you! I really enjoy reading the reviews and don't worry, why would one sleep when one could write? Let's just say I've been keeping up with my writing, and there won't be a shortage of chapters anytime soon! Okay you probably want to stop reading this and get to the chapter, long answer I know) for reviewing! A thanks as well to those who have followed and favorited! Now let us continue shall we, this ship won't sail it self! (or will it?) ;)**

* * *

_Absorbed with the sounds of the ocean and his ship, it took Dean a moment before he heard something else that caused him to open his eyes. Slowly, the pirate turned his head to look at Castiel._

"_Son of a bitch," Dean whispered with wide eyes at the sound of the former sailor snoring softly, his hair covering his closed eyes while his chin was tucked into his chest. Unable to stop himself, Dean chuckled quietly, trying to hold in his usual loud laughter._

_And for a while Dean allowed it to remain that way. A beautiful night sky rested above them while the ocean and the Impala sang together; joined with Castiel's snoring. _

_Never had Dean felt so at home._

* * *

Heavy eyelids slowly opened as Castiel began to wake up. He kept himself curled up as his eyes opened, confusion settling in at first. The first thing that came into sight was the familiar iron bars. It took a moment of looking around for Castiel to realize that he was back in his cell, minus one bench, curled up on the floor. The former sailor had started to raise himself while looking around, his forearms supporting him when he began to rise at first. But at the recognition of his surroundings, Castiel dropped himself back onto the floor completely.

Rolling onto his back, Castiel stared up at the ceiling that was the color of shadows; just like the rest of the pirate ship. Subconsciously the former sailor's hands curled into fists, memories of last night flashing before him. But then his hands unclenched as he remembered falling asleep, and Castiel could feel the color rushing to his face.

Of course he hadn't meant to fall asleep, but he had been so tired, so done with trying. The energy had been pulled out of him when he sat down on the steps, and Castiel almost flinched as he remembered almost crying. And Dean had been watching the whole time! Then the pirate had started talking to Castiel, but he was just so tired. With the ocean playing in the background, and Dean's voice being so soft, the former sailor had easily been lulled into sleep atop the stairs.

Castiel groaned, wrapping an arm around his face and covering his eyes. What a child, having a breakdown like that, even begging! Not only did his cheeks burn with embarrassment, but with shame.

_A Novak never begs_, a voice that wasn't his own growled in his head. A small shiver passed through Castiel's body at the sound of that voice. Slowly Castiel lifted his arm off of his face, eyes blinking several times.

_There was no need to delve into that past right now_, he thought to himself; one breakdown was all that he wanted to go through aboard this awful ship.

At the mention of the _Impala_, Castiel managed to sit up, his abdomen still sore from the blow Dean landed. Scooting over to the wall, Castiel leaned against the familiar dark wooden boards. His eyes glanced around the room that he's observed over a hundred times, trying to find something new that he somehow didn't notice before.

* * *

_Nine Days Previous_

Gabriel's eyes stared at the vibrant blue sky above him. An arm draped over his forehead, the older brother lay on the bottom of the lifeboat. For awhile he had rowed, the idea of getting Castiel out motivating him to row for as long as he had.

But as the morning sky greeted him, so did the exhaustion. His arms screamed from the constant pulling they had accomplished, and his back sore from his time sitting on one of the benches. The water constantly rocking the boat annoyed Gabriel, but he also found it slightly soothing once he had stretched out on the bottom of the lifeboat.

Closing his eyes, Gabriel immediately thought of his little brother, Castiel hugging his knees as he sat in the brig. But at first it wasn't just Castiel, it was a younger, smaller Cassie. The little boy that Gabriel had watched over and cared for for years; the vision almost broke the elder brother's heart.

His thoughts were interrupted though as the water rocking the boat seemed to pick up, getting rougher and larger. Curiosity bubbling inside of him, Gabriel raised himself from his previous relaxed position, despite his body's protest.

Golden eyes grew wide at the sight of the Royal Navy ship, the _Vessel_, heading towards his small boat. He could just barely make out the sound of human chatter, the distant ringing of the bell that came from the mighty ship. Gabriel wanted to give a shout of joy, he was saved! And more importantly, he could get Castiel back.

Once the _Vessel _had reached his own tiny lifeboat, he painfully rowed to the wooden boards that jutted out, forming a ladder to climb up. He ignored the staring eyes that looked down upon him over the railing as he gradually scaled the ladder. Reaching the very top, a calloused hand reached out and helped pull him onto the deck. Immediately the elder brother collapsed, leaning back against the railing. Closing his eyes, the brother took a moment to breath; he had made it.

"Gabriel?" a familiar voice spoke into his ear, the person crouching down near the tired man.

"Don't worry, I didn't get on this ship just to see your lovely face and faint from its beauty, Inias." Gabriel managed to croak from his dry throat, smiling as he heard Inias laugh and almost could imagine the sailor rolling his eyes. At the thought of his dry throat, Gabriel cracked an eye open to look at the familiar face.

"You got any water perhaps? I don't know how you all manage to do this whole sailing thing without getting parched," realizing that he could go on, Gabriel ended his sentence and continued to stare at his friend with his one golden eye. Inias nodded, and quickly passed the elder Novak a canteen.

Once Gabriel had his fill he gratefully handed the now lighter canteen back to its owner, and used the railing for support as he stood up. The curious onlookers had dispersed once they realized that it was Gabriel, although he could hear the buzzing of chatter among them, theories or ideas entering their talks as to why the head of the guard was out at sea.

Inias stayed by his side, watching to make sure Gabriel didn't fall or collapse again. At the sight of his friend's worry a smile was pulled from his lips. Gabriel rested a hand on his friend's shoulder.

"Where's Zachariah?"

"Right here, Mr. Novak," a voice called from his side. With a turn Gabriel's eyes met with Zachariah's cold, calculating cold blue eyes. Blue eyes that were so different from Gabriel's little brother, eyes that could never comfort somebody. But Gabriel knew this, he knew that Zachariah was a man who is full of nothing but arrogance, calculations, and worst of all was the man that he admired, the one he would carry out orders for without a doubt.

Swallowing his burning hatred for the man, Gabriel walked up to the Royal Navy captain.

"Captain," Gabriel gritted out, trying to contain the anger that was beginning to seep through.

"Gabriel, always nice to see a familiar face out here. Although, I don't remember you being quite the seafaring type," a cat-like smile appeared on Zachariah's face, and immediately a small shiver ran down Gabriel's spine. But he remained cool, matching Zachariah's fake smile with his own smirk.

"Well sorry if staying in the same place in the middle of nowhere doesn't sound so appealing," Gabriel countered before his eyebrows drew together.

"Anyways, I didn't come out here on choice. I got info for your little crusade to catch Dean Winchester," out of the corner of his eyes he could see Inias raise his eyebrows slightly, and Zachariah's eyes immediately lit up. But the captain crossed his arms, looking around the ship.

"And just how did you acquire this information?" The older man inquired, his attention now back on Gabriel.

"Because I was just on that blasted ship along with my little brother," Gabriel stated, watching as both Inias and Zachariah's eyebrows were raised and their eyes were wide with surprise.

"How'd you get out?"

"Where's Castiel?" Both of the seafaring men asked, and Zachariah cast an annoyed glance at Inias, who blushed slightly and lowered his head to stare at his interesting shoes.

"How'd you get out?" Zachariah asked again once he locked eyes with Gabriel once more.

"Because of Castiel, he managed to get us out of the brig, and then gave himself up so I could sneak out. So now here I am, and I have an idea where they and my little brother are headed."

Gabriel almost felt disgusted with the look in Zachariah's eyes, but he remained collected, his eyes hard and determined. Noticing this, Zachariah cleared his throat.

"Well then, I believe we're on the same team again Gabriel. Synergy at its finest," the captain smiled, while Gabriel narrowed his eyes ever so slightly.

"So it seems," he muttered, and Zachariah reached out with one of his arms. Together the two shook, both of their grips forceful and tight. Maybe it was an amicable gesture, but the two both knew that there would never be such a thing as friendship between them.

_We're on our way_, Gabriel thought as the two made their way to the captain's quarters.

* * *

Dean groaned as a knock at the door woke him from his short-lived slumber. He watched with half-opened eyes as the door opened, letting in more of the morning sky into his office.

"Winchester," the familiar voice of Balthazar greeted him as the captain rubbed at his face, trying to rid the sleep from his eyes.

"Yeah Bal what is it?" Dean asked groggily, yearning to close his eyes again. Glancing up at the quiet first mate, he realized that Balthazar had a smirk on his face.

"Did I interrupt your beauty sleep, damsel?" the first mate teased. Dean sat up straighter, narrowing his eyes with an obvious glint of annoyance shining in his green eyes.

"You play a terrible hero," Dean muttered, trying to hold back a yawn that was forcing itself up his throat. He tried to ignore the playfulness that still shone in Balthazar's eyes that made him want to smile, his friend seemed to never be completely serious.

"That's your own opinion," Balthazar countered, "but sadly I didn't come here to point out that my damsel in distress is lacking in beauty sleep. We've reached Sioux Falls, so whenever you want to come out we'll be ready." Dean nodded and Balthazar began to walk back towards the door, but a thought crossed Dean's mind and he caught his first mate's attention.

"You tried to help Castiel out last night, didn't you?" honestly Dean wasn't angered, after all he had still won, but he was just curious if his theory was true. Balthazar turned around, one of his dazzling smiles plastered on his face.

"Now what would ever make you think that I would try to level the playing field?" His first mate inquired innocently, although the look in his eyes told otherwise. Shaking his head, Dean grinned at his friend with eyes that were now awake and vibrant.

"Okay, just checking. Get everyone organized, keep a couple on deck to watch the ship. I'll be out in a few."

Confirming that he understood with a nod, Balthazar winked at the pirate captain before making his way out of the captain's quarters.

Once Balthazar had made his leave, Dean leaned back into his chair. The captain began to feel the beginnings of his starvation for sleep. Between sailing and planning during the day along with Castiel's and his games at night, sleep was a rare form for Dean to take on. But as much as the pirate craved it, he was also fine with keeping things the way they were. Releasing a small breath, Dean rested his head against his left hand, his mind drifting off to his daring midnight escapades.

At the thought of his and Castiel's game, Dean smiled as he remembered how the former sailor had fallen asleep last night. Apparently he wasn't the only one aboard his ship that was tired. What surprised him more was that Castiel was such a heavy sleeper that he didn't wake up when Dean had brought him back into the brig. Then again, a lack of proper sleep could do that to anyone.

Rubbing a calloused hand over his face, Dean got up from his chair, the stiffness evident in his back. He released a sigh as he tried to rid himself of his sore back. Even Dean knew that sleeping in a chair would never be comfortable in the mornings, but he did it anyways. It was his father's chair, and somehow it felt reassuring whenever he ended up sleeping in it; as if his dad was still there.

Sure the man had his problems, but so did every other person on this planet. And Dean could never criticize his father of his faults, hurtful as they could be at times. Despite everything that man put Dean through, he just didn't have the room in his heart for hate for the man. There was already plenty of that sewn into him, hard as he tried to ignore he knew it was there.

Realizing that Dean had been standing in the exact same spot with his thoughts gradually nearing the steel trap, he quickly tried to drown out the possible release by heading towards the door. His hands clenched and tightened several times before Dean turned the doorknob and walked into the morning sky. Blinking several times, the captain tilted his hat down a bit to provide a bit of shade for his face. He noticed most of his crew on the deck, most of their attention drawn to the stretched out town that lay before them.

A wide, roaring waterfall that lay at the back of the town gave Sioux Falls its name. The water that was carried from it flowed and snaked its way across the town before pouring into the ocean. Lush, green trees and fauna caked the land, almost hiding the intricate design of houses, shops, and other buildings that were scattered about the town. It was beautiful in the daytime, but Sioux Falls truly shined at night, and quite literally. Light sources of various kinds would be spread out, along with being behind the noticeable trademark of the town. A sight that was great to behold from the sea, when one could see almost the entirety of Sioux Falls.

Admiring the view of the town, Dean walked up the steps that led to the wheel, standing next to Balthazar.

"Takes you back, doesn't it?" Dean asked, his eyes glancing over to his first mate whose eyes were focused on the approaching town. Balthazar was quiet for a moment, something that was new to Dean's ears.

"Yeah," his friend managed before clearing his throat, "Dean, it most definitely takes me back." A sincere smile formed on both their faces, memories of smaller versions of themselves floated around in both of their heads.

"You were such a moron," Dean commented, his eyes still trained on Sioux Falls.

"And you're still one," Balthazar retorted. With just another quick glance the captain could see the usual mischievous, playful glint that shone back in his first mate's eyes. Dean playfully shoved Balthazar's shoulder.

"Bring her into port," the captain ordered before making his way down the stairs and headed towards his gathered crew. Shifting their attention from the town to Dean, he waited for all eyes to be focused on him.

"Okay, we're going to be here for only a little bit so make sure you take care of whatever business you need to take care of before we leave again. Any questions?" At the sound of only whispering passing between a few, Dean clapped his hands together before singling a few of the crew.

"Charlie, Kevin, and Garth. You guys stay on ship, watch over her for me okay?" The three seemed a bit disappointed in the aspect of not getting to enter the town. But they didn't complain, only nodded before dispersing along with the rest of the crew. He would give them a moment to grab whatever they desired to bring with them.

After the crew was ready, and Balthazar brought the ship closer to the port, Dean ordered for the anchor to be dropped and soon the ship was docked parallel to the port. Casting a final glance at the _Impala_, Dean began to make his way off the pier and into the town, along with a gradually thinning out crew. But just as he was crossing one of the many bridges, a hand rested on his shoulder.

Dean turned to face Balthazar, who stood behind his captain.

"Just what is it you came here for, Winchester?" Dean almost wanted to share with Balthazar, one of the few he knew he could really talk to if he so desired. But the captain had no desire to share his dark tale just yet, so he just shook his head with a sad smile forming.

"Balthazar, I know you wonder more than the others as to why I left. But that's something I can't, or won't, talk about just yet. Let me conduct what I need to do here, and if I find what I seek then maybe I can finally shed some light. Just trust me for now, can you do that?" Dean looked at his first mate, whose eyes were searching Dean's.

"Always," Balthazar answered while squeezing Dean's shoulder. But quickly the first mate changed back into his usual form, a grin placed on his face. "Just don't try to do something mad like the moron that you are." Smiling back, Dean winked at the fellow pirate before turning away, throwing back an answer as he continued to cross the bridge.

"Where's all the fun in that?"

* * *

**Exciting things are heading our way people, things I've been looking quite forward to honestly! Please review, follow, or favorite if you enjoyed; I always appreciate it :D Have a wonderful day and I'll see you at the next installment!**


	12. Familiar Gals

**Next chapter! Thanks to DeerTopus C. VonZenHousen(perhaps…), Kather-Swine( I almost wanted to say carried when I wrote it, but I decided to leave it to the reader's imagination. And stuff's about to get real 0.0), Marmar( I know you posted your review earlier, but I'd rather address you now. But where's the fun if I can't tease you guys like that?), mywarisalreadywon( glad to provide such wonderful dreams, I'm sure some of those characters will be making an appearance ;), and Air Guitar Pixie( Ahh Sammy, I'm going to leave it at that. As for Sioux Falls… I'm going to let the chapter speak for itself! Thank you and I'll do my best, no pressure!) for reviewing! A thanks as well to those who have favorited and followed! Now let us continue on with our lovely pirate crew :)**

* * *

"_Balthazar, I know you wonder more than the others as to why I left. But that's something I can't, or won't, talk about just yet. Let me conduct what I need to do here, and if I find what I seek then maybe I can finally shed some light. Just trust me for now, can you do that?" Dean looked at his first mate, whose eyes were searching Dean's._

"_Always," Balthazar answered while squeezing Dean's shoulder. But quickly the first mate changed back into his usual form, a grin placed on his face. "Just don't try to do something mad like the moron that you are." Smiling back, Dean winked at the fellow pirate before turning away, throwing back an answer as he continued to cross the bridge._

"_Where's all the fun in that?"_

* * *

After getting bored of constantly looking around the room for something new that wasn't there, Castiel's attention was drawn to the sounds above him. It seemed that there was something going on, what he didn't quite know, but there was definitely a lot more activity happening above him than there usually was.

It was when Castiel heard the familiar sound of an anchor dropping that his curiosity was ravenous, and he tried to peek through one of the small holes that had been in the wooden boards. As he tried to look around he was met with a joyous sound, people! He could hear the sound of people talking, some shouting others and others just talking. They were docked!

Castiel felt his heartbeat quicken, if there was anytime to get off of this blasted ship, it would have to be now. Regretfully pulling himself away from the wall, his eyes glanced all around the room. Already he had combed through his cell and learned that there wasn't anything that would assist in his leave in anyway. Running a hand through his dark brown hair, the former sailor tried to think. He squeezed his eyes shut, both of his hands atop his head as he tried to focus, to find a way out.

But nothing came to him, because for ten days not only had he tried to escape, but Dean Winchester easily learned how the former sailor got through his defenses and was able to take the precautionary measures that he couldn't use the same strategy twice, save for Balthazar's mistake.

Frustrated, Castiel let out a growl and lashed out with a foot at the wooden boards that formed the side of the ship. Collapsing to the ground, Castiel sat down in the middle of his cell. Blue eyes found themselves gazing up at the familiar ceiling, as they usually did. And that's how Castiel sat for a while, his mind blank while his eyes locked onto the ceiling, noticing every little detail about it. Scooting over to the side of his cell, the former sailor rested into the corner, iron bars meeting with wooden boards forming the spot that he sat in.

_Novaks don't give up_, a voice that sent a shiver down Castiel's spine growled from inside his head. Quickly his heartbeat began to speed up, it racing at the sound of that voice.

_He's not here, he's not here, he's not here_, the former sailor chanted to himself, trying to block out the deeper, vicious voice that still seemed to be growling at him. Opening eyes that he had clenched shut, Castiel looked around the room again. His eyes dug into every little corner, anything in eyesight that he could use. As much as Castiel didn't want to hear the voice, he knew at least one thing that it spoke true of.

Hell will freeze over before he was going to give up trying to get off of this structure of floating wood.

* * *

Dean found himself walking all over the town, to be honest he wasn't quite sure if she would be here at all. Just rumors was all that the captain had to go off of, but rumors were better than nothing at all. As much as Dean wanted to admire the town, enjoy the delicacies, his purpose for stopping at Sioux Falls conquered all other possibilities.

His eyes tried to glance at every person he had walked by, he was lucky enough to know what the woman looked like. But it was always her location, the woman seemed to never sit still. Which wasn't particularly helpful for him, but he couldn't change her lifestyle for the sake of his own benefit.

Entering one of the main streets that ran through the town, Dean scanned the entire group of people, looking for familiar long, dark curly hair or her green eyes. Ignoring the odd stares that he received from others as he walked along the street, the captain kept his eyes searching, looking at every possible face. Finally his eyes looked up ahead of him, and despite the distance Dean immediately recognized the familiar form of Pamela Barnes.

"Pamela!" He shouted, and somehow the woman heard him. She turned her attention towards the pirate, a look of surprise on her face at the sight of Dean Winchester. Smiling, she tried to reply over the hustle and bustle of the crowd, but her words were lost in the thicket of others. Shaking his head, Dean began to make his way forward when all of a sudden a hand gripped his shoulder and pulled him into the far less crowded alleyway.

"What the hell?" Dean barked before his eyes locked onto Balthazar's. The first mate held Dean against one of the sides of the alleyway, and Dean noticed the look in his eyes.

"Balthazar what's wrong?" he inquired, the first mate still quiet before he cleared his throat.

"We may have a problem."

"Would you like to clarify?"

"I was heading back to the ship, not much I really needed to do here anyways. But there were these women near the _Impala_, and one of them said that she knew you."

Dean rolled his eyes, "I get that a lot, what's the worry?" but he was disturbed by the way Balthazar was anxious, his eyes flicking back to the main street, still holding onto Dean.

"I'm serious Dean, they didn't look like good news. And when I mean knew you, I mean she really _knew_ you."

Dean stared at Balthazar, still a bit doubtful of his friend's worry. But rarely was Balthazar this uneasy, this perplexed.

"Okay, I understand," Dean glanced down at the grip that Balthazar still held him with, "you can let me go now Bal."

The first mate seemed to just realize how tight of a grip he had held Dean with, and he immediately let go of the captain as if he was burned by the touch. Resting a hand on his friend's shoulder, Dean tried to reassure his friend.

"I'm sure it's nothing," Balthazar was about to protest but Dean raised a hand for silence, "but let's go check it out, okay?" Relieved Balthazar nodded and walked ahead of the captain, making his way through the busy street and towards the pier. As Dean followed, he glanced at where Pamela Barnes had stood, now a vacant spot in the crowded street.

"Damn it," Dean muttered before catching up to Balthazar. Hopefully she didn't decide to skip town at the sight of the Winchester, she didn't seem upset or mad which was a good sign; at least Dean hoped it was.

Together both Dean and Balthazar walked side by side down the curvy roads and across the bridges of Sioux Falls. Constantly Dean found himself glancing at Balthazar, who was walking with a fast pace and seemed to repeatedly clench his hand into a fist before releasing it.

Finally the two reached the gate that led into the pier, and Dean found his eyes wide with surprise.

* * *

Castiel found the lack of silence on the boat slightly disturbing, but he quickly realized that most of the crew probably went onto land. So as he decided to enjoy the bit of silence that came with the lack of crew, Castiel stood up from his corner and began to walk around the cell. He tugged at a couple of the rusted iron bars, trying to see if any of them were loose or weak. But the bars were immovable, hard as the former sailor tried to pull one loose.

Soon he was just simply walking aimlessly around his cell, trying to find something to do or a way out. Either was a good reason for him, which one he was acting upon was something that he wasn't quite sure about.

He paused, the quiet enveloping him as he thought he had heard what sounded like a splash coming from right outside. Castiel shook his head, it was a port, there was bound to be all sorts of noises like that going on. Yet the suspicious feeling that was growing in the pit of his stomach nagged at him, and he remained silent.

Nearly jumping as he heard someone shout before another splashing sound followed, Castiel's heart began to race. He tried to look out through his peephole, but all he saw was the port, a few women standing near the boat while the rest of the pier seemed to be almost empty save for the other ship that rested parallel to the _Impala. _Stepping away from the side of the ship his eyes glanced up towards the ceiling and he tried to think of what was happening on the deck above.

_Just what was going on up there?_ His curiosity was screaming at him when he heard the last of the splashes, which added up to three total. Footsteps began to increase above him, and hundreds of possibilities were racing through his head as his eyes were glued to the ceiling above him.

His ears perked up at the sound of the anchor being lifted from the water, and worry began to seep into Castiel.

_Surely they aren't already leaving? They just got here_, Castiel reasoned with himself. Suddenly the former sailor wasn't quite sure as to just who was above him on the ship.

* * *

Dean looked to see the wet forms of Garth and Kevin on the pier, Charlie climbing up to join them. And there sat the _Impala_, its anchor being pulled out of the water. Dean's eyes looked at whoever was on his ship, and he felt himself freeze once he made out a particular form in the many that were now on his ship.

The captain turned towards Balthazar, who was watching with shock in his eyes, his mouth hanging open as if to say something but no words came out.

"Balthazar," Dean gripped his friend's arms, forcing the pirate to face him, "listen carefully. Gather up the crew, and find another ship. I don't care how, just get another ship. You're in charge until I get back." Balthazar stared at Dean as the pirate captain shed his coat, dropping it onto the pier.

"Where are you going?" Balthazar questioned, his attention split between the _Impala_ and its captain.

"Probably nowhere good," Dean answered before racing towards the other ship that had been parallel to the _Impala_. He raced up the ramp, dodging past sailors that cursed at him and tried to stop him, his eyes locked only on his ship. Drawing his sword as he reached the very top of the ship, the pirate grabbed onto one of many ropes that were near, and with one clean slice separated it from its knot that held it down.

With speed Dean sheathed his sword and grabbed onto the rope with both hands, standing on the railing. The pirate gave a look of uncertainty as his eyes remained trained onto his ship, which was slowly leaving port. His eyes were met with familiar brown eyes, and he narrowed his eyes at her.

"What the hell," Dean muttered to himself before jumping off the ship and away from the sailors that watched in awe as Dean swung from the ship and over the pier, reaching the edge of the _Impala._ Letting go of the rope, the pirate desperately grabbed at the dark railing that ran around his ship, bringing his feet up to the small space between the rail and the edge of the deck. Hauling himself over, Dean landed on his feet and brought his head up, meeting the faces of several women who surrounded him, swords and pistols drawn and focused on him.

A thick, country voice called out from behind the rest of the crew.

"Ballsy as always, Dean. Good to see you still haven't lost your touch," he watched as the crew parted, making way for their captain. The leader took slow, calculated steps as she sauntered up to where Dean stood.

His eyes met with the woman with dark, curly hair that tumbled around her round face. A smile that was by no means innocent was placed on her face, one hand resting on her hip, the other resting at her side with a sword in her hand. Her dark eyes twinkled before they shifted to pure black.

"Meg," Dean acknowledged with narrowed eyes, resentment evident in his voice as he spoke her name.

"Hi again," Meg greeted, her eyes changing back as she took another step towards him. Dean remained where he stood, his back almost touching the railing that rested behind him.

"What are you doing here, Meg?" Dean asked while both of their eyes remained trained onto each other's. Meg didn't answer at first, instead turning towards her crew.

"Search the ship, make sure there isn't anybody else on here." Dean watched as three of Meg's crew split off from the group, and he knew that a discovery would be made soon.

Although Dean had jumped onto his vessel because he needed to make sure it was Meg, another part of him had done it because Cas was still on the boat; and he couldn't just leave the man to the sharks after not killing him. With eyes flaring with rage Dean and Meg continued to stare at each other, a smile dancing on the pirate's face while Dean's face was stone. A cold laugh erupted from Meg, and a smirk replaced her previous expression.

"What's a matter Dean, surely you didn't think you'd seen the last of little ol' me?"

* * *

Castiel did a sharp intake of breath as he heard heavy footsteps descending down the stairway and into the crew's sleeping area. His ears stretched as he listened, hearing one pair of footsteps heading towards the opposite hallway while another opened the door and began to make its way towards the brig.

The former sailor remained rooted to the spot as the door to the brig opened, revealing someone that he didn't recognize. Standing in the doorway was a woman, her golden hair straight and bright compared to her dull gray coat that ended just where her boots started.

Castiel tilted his head slightly at the sight of an unfamiliar face, although the theories that he had been considering narrowed down to only a couple.

"Who are you?" The former sailor requested, his eyes scanning her confident form. A smug look appeared on the girl's face.

"I should be asking you the same thing," the stranger replied, her eyes glancing around the rest of the brig. "Stay there," she ordered with light in her eyes as she turned around and raced out of the room. Castiel was about to shout to her, but she had exited too quickly. An uneasy feeling began to fill the former sailor, he was pretty sure that the woman wasn't here to release him.

Silently Castiel remained where he stood, trying to listen to see if he could hear anything above him. But there wasn't anything that Castiel could hear, which bothered him a great deal. The former sailor walked up to the door, testing it a couple times. Heart racing, Castiel stood back and kicked at the door. After the third kick, he was beginning to feel that he could probably somehow break it, but Castiel went rigid at the sound of approaching footsteps for the second time. Desperately the former sailor kicked at the door two more times before he heard the door to the brig opening.

The same woman stood before him, and he noticed the way she stared as his chest rose and fell with the weighted breaths that he took. Her eyes flicked away from him and towards the door, which showed the signs of Castiel's attempts to break the door down.

"Am I that terrifying?" The familiar smug look was back on her face in seconds. Raising her hands, the woman revealed keys in one hand, a pair of shackles in the other. Castiel's brow furrowed at the sight, this was definitely not an ally. Quiet for a moment, the two stared at each other, the stranger leaning against the door frame while Castiel stood silent, save for his breathing.

"Are those necessary?" He finally asked, and he watched as the woman smiled slyly.

"Orders, kiddo. Someone wants to meet you," she answered with a small shrug before walking over to the cell. Watching as she began to try the different keys that hung on the key-ring, Castiel calmed his breathing, his heart. Once they both heard the proper key click into place, the stranger opened the door. One hand gripping the handle of her sword threateningly, she raised an eyebrow as a challenge for him to try something.

Raising his hands in a gesture of surrender, Castiel walked up towards the unfamiliar woman, who kept her gaze challenging and intimidating. She tossed the handcuffs to the former sailor, who caught them while keeping his eyes on her.

"Put them on," she ordered, drawing her sword out slightly from its sheath. Sighing, Castiel glanced at the woman, his head slightly tucked in while his eyes remained stuck on hers.

Suddenly the former sailor charged at the stranger, who immediately began to draw her sword but was too slow before drawing it out completely from its sheath.

Tackling her to the ground, Castiel attached one of the handcuffs to the woman's wrist while trying to keep her pinned to the ground. Looking up, Castiel reached over, attaching the other part of the handcuff to the cell that had been across from his own. Immediately Castiel jumped off of the woman, who pulled at the handcuffs and swore.

"Guess they were necessary," he agreed to the woman as she turned to him with narrowed eyes. She reached over with her other hand and tried to lash out towards the former sailor with her sword, but he quickly dove out of the way as the sword reached where he had previously sat.

Standing up, Castiel didn't look back at the woman as he turned and walked out the door, closing it behind him. With calculated steps, Castiel slowly walked through the hallway, his attention focused on the deck above him. Once he reached the door, Castiel turned the knob slowly, memories of Gabriel's daring escape playing in the back of his mind.

But then the former sailor froze, frowning as he was met with nothing but silence. Especially because of the fact that he left someone chained to a cell back in the brig; she should be screaming her head off, trying to gather attention, right? Then the image of keys floated into his head and Castiel dragged a rough hand over his face, his eyes looking up as he cursed at himself.

"Stupid, stupid. She's already out," Castiel muttered, slowly turning around. Before he had time to react the woman smirked as she swung something at his head, connecting with his temple. The former sailor collapsed near the door, his head throbbing.

"Dumbass," he heard the woman say as she bent down, something metal clinking in her hand. It was a great effort for Castiel to keep his eyes open, and he found himself losing as his eyelids gradually shut down, darkness embracing his vision.

* * *

**I don't know if any of you watch Sherlock, but if you do, squint really hard at this story and you may be able to see a couple of references! Please review, favorite, or follow if you want to!**


	13. Windows Into Oblivion

**Ello again! You all ready for the next installment? Well first, thank you to Air Guitar Pixie (Yesh Meg! But actually the woman with Cas is not quite Meg… Close guess but that actually isn't the parallel that I was going for, though it is a fair guess), Kather-Swine(oh yeah….complete shame… if only I had done that.. but don't worry… who knows, plenty of time, you catch my breeze? ;), Akayuki Sawada( yup, but can you blame a guy for trying?), mywarisalreadywon( Wow, to get such a reaction is quite lovely to see/read! I'm glad your enjoying the tale as much as I am!), and DeerTopus C. Von Zenhousen( yes! I put my own twist on it but they are here in this universe. Your theory of course, is just as plausible as everyone else that writes or thinks up there theories. I'll leave it to the characters of the story to see if that would ever happen between the two ;) for reviewing! A thanks as well to those who have followed and favorited, I always love seeing more people join our little own crew! Now, enough with the formalities, let us continue!**

* * *

_But then the former sailor froze, frowning as he was met with nothing but silence. Especially because of the fact that he left someone chained to a cell back in the brig; she should be screaming her head off, trying to gather attention, right? Then the image of keys floated into his head and Castiel dragged a rough hand over his face, his eyes looking up as he cursed at himself before shaking his head._

"_Stupid, stupid. She's already out," Castiel muttered before turning around. Before he had time to react the woman smirked as she swung something at his head, connecting with his temple. The former sailor collapsed near the door, his head throbbing._

"_Dumbass," he heard the woman say as she bent down, something metal clinking in her hand. It was a great effort for Castiel to keep his eyes open, and he found himself losing as his eyelids gradually shut down, darkness trying to overwhelm him._

* * *

Castiel gave a grunt as he felt a tug, someone trying to pull him. His eyes fluttered open, and he immediately screwed them shut as spots gathered in his vision and his head screamed. Then he felt the tug again, someone pulling up on his arms which were behind his back.

_Behind my back? _Castiel thought as he cringed when his head gave another cry of pain. But then he remembered someone calling him a dumbass, which at first Castiel found odd until his mind flooded with the previous events. The stranger, their fight when he left her in the brig, and then she was out and then she had hit him with something. He remembered falling, but he didn't remember his arms resting on his back.

Experimentally, the former sailor tried to move his hands, but then he rolled his head against the door once he felt the cold metal of the handcuffs biting into his wrists.

"Damn," he muttered, but his attention shifted when he heard someone snort. His mind and eyes swam, still blurry from the solid blow that the woman had delivered, but Castiel managed to turn his head. Blue eyes looking up, his gaze met with the confident, victorious look of the stranger, who had a thin smile while she stared down at him with a single-raised eyebrow. Brushing a strand of hair from her face, she crossed her arms while maintaining her staredown with the former sailor.

"Are you done, dumbass?" Castiel's jaw clenched while his eyes narrowed at the smug woman. Refusing to answer, the former sailor pressed his lips together, forming a thin line as he could feel the anger beginning to rise inside of him. But his face fell and he dropped his eye contact once he cringed in pain, grudgingly releasing a small groan as his head throbbed. Eyes shut, Castiel formed both of his hands into fists, riding out the waves of pain that came from his head.

He barely noticed the sigh that came with the woman as she stepped forward, bending down and grabbing him by his upper arm. She tugged on his arm, but Castiel refused to budge, out of both pain and his own stubbornness.

Releasing a breath of annoyance, the stranger reached over and grabbed a fistful of Castiel's hair before pulling it back roughly, receiving a grunt from the former sailor. Leaning down, Castiel could feel her breath against his ear.

"Get up on your feet now, we don't have all day princess," she hissed before dropping his head; it fell back down to the floor and Castiel held back another groan of pain by gritting his teeth. As the woman maintained her hold on his upper arm, slowly he rose up, collecting his feet under him before he managed to stand up, taller than the smaller woman by a decent amount.

Opening the door, the stranger kept an iron grip on Castiel as he half-followed, half-stumbled behind her. He didn't admit that her grip on him helped him from tripping on the stairs, instead he turned his head with closed eyes as she opened the door and bright morning light swallowed his vision.

Once his eyes adjusted, Castiel glanced around the deck, his eyes sweeping across it and the other strangers that were running around, until his focus landed on a couple of women who were holding back an irritated Dean Winchester. The woman who held onto him began to walk over there, pulling him along.

A particular woman that was standing in front of Dean turned as she heard the approaching stranger and Castiel. Immediately the former sailor froze, his feet rooted into the wooden boards as he saw the woman.

Along with her pitch black eyes.

* * *

"What's a matter Dean, surely you didn't think you'd seen the last of little ol' me?"

Dean surged forward, green eyes burning as he was restrained by two of Meg's crew. They forced the pirate to his knees, while the others stared with raised swords and pistols. The female captain's wide grin stretched further, and she turned to her band of pirates.

"Get yourselves organized, regular stations. Someone take the wheel and just get us away from that forsaken town."

Pulling at the two pirates' grip, Dean tried to escape from their hold. Meg nodded to one of the pirates, and he saw the black-haired woman pull out a pair of handcuffs. Clenching his jaw, Dean tried again to pull free from the two. But the two held strong, and Dean's wrists were met with the tight, cold metal that bit into his skin as he tested them. Dean dropped his eyes, not wanting to look into the face of Meg, not wanting her to see what was leaking out from his steel trap and tainting the look in his eyes. But Meg noticed, and quickly she realized what Dean was most likely thinking of.

"You know, this almost looks familiar," Meg sang, and the captain walked up to Dean, her fingers wrapping around the top of his throat. They weren't trying to choke the life out of him, instead lifting his head up so his eyes stared into her own. But his gaze was drawn to a woman that rushed up from one of the staircases and towards Meg.

"Captain," the blond-haired woman interrupted, and Dean immediately released a breath he didn't notice he had been holding when Meg let go of him. The captain turned to face the unfamiliar pirate.

"What is it, Ruby?" Meg asked, obviously annoyed at having been disrupted from her business.

"There's a man down in the brig," the pirate named Ruby answered, her eyes drifting slightly to the man on his knees before they focused back on her captain.

Meg turned and faced Dean, hands on her hips as a smile was shaped by her lips.

"You've got a man in the brig?" her voice was full of curiosity and surprise. Dean refused to meet her eyes, looking straight ahead. She bent down and leaned forward, whispering into his ear.

"That's not the Dean Winchester I know," her eyes were lit up with pleasure at the sight of his face falling slightly, and Dean turned his head away so he couldn't look at the captain. Smiling to herself, Meg turned back towards Ruby.

"Go ahead and bring him on up, I want to meet the unicorn," Meg commanded and Ruby nodded before turning around and heading back towards the stairway. She paused as Meg called out to her.

"Don't forget to secure his hands," she ordered before turning back to face Dean again. This time she bent down, her eyes level to his own as he continued to look away.

"Now Dean, why the sudden acts of kindness? You think that maybe it'll get rid of all those little dark thoughts that are scratching at your head?" She leaned forward, Dean's eyes finally locking onto her dark eyes. With a smile Meg's eyes remained full of confidence and enjoyment as she continued to mock the pirate. Her voice was quiet and vicious as she spoke.

"You can never take it all back, Dean. All of that blood is on your hands. Your brother's blood too," Meg relished in the broken look in Dean's eyes, how his face faltered. But she was almost impressed as Dean recovered, and he jerked forward despite the strong resistance that it was met with by the two that held onto him.

Pulling his head back, Dean threw his head forward, connecting with Meg's forehead. The captain cursed as she stood up, and Dean smirked at the look of vexation that appeared on her face.

"I don't break that easy, bitch," Dean snarled, his vibrant green eyes blazing with defiance. But Meg only faltered for a second before the smug look appeared back on her face.

"But you can break; we both know it," she countered.

Their attention was pulled as Dean and Meg's eyes were drawn to the stairway. Ruby appeared first, annoyance written all over her face. Dean's eyes traced over her arm, and to her hand that gripped onto the sleeve of a familiar tan coat.

Looking up, Dean took in the injured face of Castiel. Blood was trickling down the side of the former sailor's head, and his eyes seemed weary along with his posture; he looked battered. Yet despite the weariness that resided in Castiel's eyes, they were tinged with anger; a look that Dean noticed seemed to always be in his eyes. Meg turned around to look at the man that Dean's eyes were locked onto.

Then Castiel immediately froze, and Dean closed his eyes and sighed. It wasn't hard for the pirate to guess that the former sailor had seen Meg's eyes change to black. For a moment Castiel just stood there, eyes staring at the captain until Ruby pulled him forward, and he stumbled behind her.

* * *

Never in Castiel's life had he seen such a phenomenon such as the woman that stood in front of him. Sure she seemed like a regular woman at first, attractive with her dark curly hair and figure. Although that was the last thing on Castiel's mind, especially considering the predicament.

But once her eyes transformed into two obsidian orbs that seemed to be windows for oblivion itself, the last thing the former sailor wanted to do was go near such a thing. The woman that had attacked him though had different plans, and she pulled Castiel forward with unexpected force. He stumbled, barely able to keep himself from dropping as he and the stranger briskly walked over to the monster in the form of a woman.

Castiel's attention drifted over to Dean, who managed to get off of his knees and stood with a stiff posture while two women stood on either side of him, his face rigid and slightly paled; Castiel assumed it was because of the sight of the monster's eyes.

"Was he leaking like that when you found him Ruby?" the woman with the black eyes asked, her eyes shifting back to a normal pair of human eyes. The stranger that had found him, apparently her name was Ruby, smirked before pulling Castiel forward and closer to the thing he didn't want to be anywhere near.

"He wasn't playing nice," came the reply.

Castiel anchored himself to the spot where he stood, his whole body tense as the woman who had the coal-black eyes approached him. His heart was racing as she stood next to him, her face only a few inches away from his own. She tilted her head up, eyes looking into Castiel's intense blue eyes. The former sailor could feel the breath of the creature hitting his face, and the silence was deafening as she maintained her position and so did he, neither of them backing down; despite how Castiel swayed ever so slightly from foot to foot.

Then the woman blinked, and when her eyelids shut a noise that was unknown to Castiel followed. She opened her eyes and again they were bottomless pits that sucked in the normality that had once been the woman's illusion. An innocent smile looked out of place as she grinned up at the former sailor.

Castiel looked away, and instead of staring at the being before him his eyes locked onto his greatest, most vexing adversary that stood to his left.

The pirate's eyes were watching the encounter between Castiel and the black-eyed woman. Once the former sailor had glanced over to him, the two focused onto each other. Castiel tried to see how Dean was reacting to the creature before him; surely he had seen the woman's eyes change.

But the only look in Dean's eyes was caution, followed by rage. What confused Castiel further was the dark, guarded look that he noticed. The only time that Castiel had seen such a look…

The former sailor was brought back to the time he and Dean had talked, where the challenge for Castiel's freedom had been made. Faintly Castiel remembered that Dean had been about to mention another person, but the pirate had caught himself and instead that same look had been haunting his eyes.

"Well aren't you two adorable," a sweet voice pulled him out of his thoughts and Castiel blinked several times. Castiel gradually brought his gaze back to the woman who stood so close to him. Squinting, his eyes fell upon the monster's and gave an inward sigh of relief at the sight of her now normal eyes.

"I beg your pardon?" The former sailor asked, confused by the woman's statement. He watched as the creature rolled her eyes.

"So he speaks," she said before sashaying over to where Dean stood and resting her elbow on his shoulder, "Well unicorn boy, what do you know of Mr. Wonderful over here?" Her eyes narrowed with mischief, she was reveling in the power she held over the Winchester. Castiel watched as the color that had begun to return to Dean's face seep out; draining him of the former confidence that Castiel was so accustomed to seeing on the pirate.

The woman noticed the way Dean reacted to her question, and her eyes lit up like a child with delight flooding into her light brown irises. She turned her attention back to Castiel, her elbow resting on a Dean's stiff shoulder.

"Ah, seems our fearless pirate isn't quite so confident now, huh? Boy, the things I've seen this man do-"

"Shut up, Meg," Dean growled, his eyes cold and dark as his whole body seemed to tremble, Castiel wasn't quite sure if it was from anger or fear. The pirate that Castiel had always found vexing and troublesome now seemed smaller, unsure of himself.

What had happened to the infamous Dean Winchester?

* * *

Meg smiled as she tilted her head at Dean. "Strike a chord, did I? Don't want your unicorn to hear about your lovely past?" Dean narrowed his eyes at the pirate, his face rigid as his jaw remained clenched.

"Why don't you cut the crap already bitch. What are you doing on my ship?" Dean challenged, quickly finding his feet and running from his previous feelings. He wouldn't let this woman break him, tease him. Meg pouted, bringing up her bottom lip in mock hurt.

"I was just remembering all the fun we had together, I thought you might want to share with your lovely friend over there." She shrugged as she lifted her elbow off of Dean's shoulder, making her way over to the former sailor. Dean watched, unsure of Meg's actions as she stood extremely close to Castiel. Dean noticed the way Castiel's eyes were looking down, watching the pirate that was almost pressed up against him with uncertainty in his gaze.

Green eyes went wide with surprise as Meg wrapped her arms around Castiel's neck, and pulled him down. Her lips met his, and Dean watched as she kissed a surprised Castiel, whose eyes were as wide as his own.

After what seemed like an eternity Meg dropped the kiss, and a grin bloomed on her face while Castiel frowned. Unphased, Meg turned away from the former sailor and stood in front of Dean.

"Well, I was in the market for a new ship. My lovely crew and I were unwillingly residing at Sioux Falls; imagine my surprise when I see this lovely little boat pull into port. All those nasty little rumors about the infamous Dean Winchester and his beloved _Impala_, well I really wanted to take her out for a spin after hearing about how it was owned by the infamous pirate himself. Especially when it was _you_ of all the little normal pirates." Meg answered, as if she hadn't been sucking face with Castiel just moments before. Dean cast his eyes towards the former sailor, who was watching the two intensely, curiosity evident in his blue eyes.

"So I assume you two know each other?" Castiel spoke up with a rough voice, his eyes focused more directly on Dean than Meg. Said woman turned, her attention back on the man she had assaulted with her lips. Dean looked at the former sailor as well, their eyes connecting. A smirk fell on Meg's face.

"Of course, me and Dean go way back!" She tossed a glance back towards Dean, who didn't react to her remark. Grinning at the pirate, Meg turned back towards Castiel.

"But I'm sure he can tell you all about it," as she faced Dean once more, the look on her face sent Dean's mind searching as he tried to decipher her message. The woman looked at the pirates that held onto him.

"Take them both to the brig," she ordered before making her way back to Castiel, who now watched her warily.

"Nice meeting you loverboy," she winked before sauntering away, and Dean watched with narrowed eyes as she entered _his_ quarters.

"Bitch," Dean muttered before he was pulled forward by the two women that held onto him. He watched as the pirate who had been holding onto Castiel lead the way, and Castiel still seemed a bit off; a small stream of blood still curving along the side of his face.

The quick trip was silent as they headed down, and Ruby opened the cell that was across from the one Dean had put Castiel in, and she shoved the former sailor in. Dean followed, the two pirates forcing him in before Ruby closed the door with a smug look on her face.

He watched as they quickly left the room, and he listened until he could no longer hear their footsteps. Turning around, Dean's attention was brought to Castiel, who was leaning against the side of the ship; his eyes unfocused as he tried to look at Dean. An uneasy feeling filled his stomach.

It seems the time for running was finally bearing down upon him.

* * *

**THINGS ARE GETTING EXCITING NO?! A side note, I imagine Ruby as the first one and Meg as the second actress who played her. I do really like the second Ruby, but I didn't want to have to continue going with lovely women with dark brown hair, no disrespect! Thank you for reading and please review, follow, or favorite if it suits your fancy!**


	14. Careful Consideration

**Why hello again! Back for another chapter, are we? Thank you to DeerTopus C. VonZenHousen(what now indeed? ;), Akayuki Sawada(head injuries and backstory, aren't they both so lovely?), masterlokiseverus159(Questions are good! Where would we be without such curiosity that you are experiencing?), Kather-Swine(wait..till..you..see...what..I..have..planned…for..the...near...future...then..your...quest...for...cozy...shall...be...reached!), fictionfarytalesfantasy4921(IS HE? A crew is certainly on the trail…guess you'll just have to wait and see ^_^), and Air Guitar Pixie(I haven't decided about angels or not, who knows? Let your excitement for the next installment rest, for here it is for readers like yourself to devour!) for reviewing! A thanks as well to those who have followed and favorited, my appreciation goes to you! Now, shall we proceed from where we left off?**

**Edit: Thank you to Akayuki Sawada for pointing out the chapter being all, well screwed up. Hopefully it's fixed now, sorry about that!**

* * *

"Bitch," Dean muttered before he was pulled forward by the two women that held onto him. He watched as the pirate who had been holding onto Castiel lead the way, and Castiel still seemed a bit off; a small stream of blood still curving along the side of his face.

The quick trip was silent as they headed down, and Ruby opened the cell that was across from the one Dean had put Castiel in, and she shoved the former sailor in. Dean followed, the two pirates forcing him in before Ruby closed the door with a smug look on her face.

He watched as they quickly left the room, and he listened until he could no longer hear their footsteps. Turning around, Dean's attention was brought to Castiel, who was leaning against the side of the ship; his eyes unfocused as he tried to look at Dean. An uneasy feeling filled his stomach.

It seems the time for running was finally bearing down upon him.

Castiel stared up at Dean, who met the look evenly. His eyelids drooped slightly over his blue eyes while he tried to fight to stay conscious. Honestly, Castiel had been surprised that he had even managed to stay standing during the whole encounter with the woman, Meg, and hearing about her and Dean.

"Dean," Castiel began as he tried to think over what happened up on the deck, his voice. But his memory was fighting against him, the most significant thing that was sticking out was when that creature had actually kissed him. With eyes wide Castiel felt the bile rising up inside of him.

"I'm gonna be sick," he said as he recalled that thing's, or woman's, mouth assaulting his own. Not the most pleasant experience Castiel had ever been through, and the bile was pushing up stronger now. Faintly he heard a grunt and feet hitting the ground, and suddenly there was a hand resting on his left shoulder.

"Meg'll do that to you," the voice of Dean Winchester jested, and the hand gripped his shoulder as the former sailor brought his head over to his right and retched.

"Well that's just peachy," Dean continued to narrate, his voice attempting to be light and good-natured. Coughing, Castiel tried to collect his feet under him to try and stand up. Dean's hand continued to hold onto him. "I don't think you should get up man, I think you may have a concussion," the pirate tried argue.

Castiel turned his head to face Dean, trying to hold back the feeling of annoyance that sparked inside of him as he met the bright shades of concerned green eyes that stared at him.

"That is not of import. The fact remains that I just emptied the contents of my stomach onto the floor next to me and would not like to continue sitting next to such an unpleasant sight or smell."

At first the pirate was quiet, his face blank as he stared at Castiel. Then Dean burst into laughter, the kind that Castiel had heard long ago, and he watched with an unfocused gaze along with a raised eyebrow as the pirate fell off of the balls of his feet and onto the floor. After what seemed like a continued stream of laughter from the pirate, he took a couple of breaths to try and calm down.

"Ah man," Dean managed as he wiped a tear that had begun to form in his eye away, "sorry Cas, but you just have the strangest vocabulary." Immediately upon the sight of narrowed eyes, the pirate collected himself. "Alright, alright. You really need to grow a sense of humor," Dean grumbled as he tried to support Castiel while the former sailor began to try and rise.

"I don't believe one can grow a sense for anything," Castiel muttered under his breath. He now stood unsteadily, deep down grateful for the support Dean was providing. Slowly the two made their way over to the other side of the cell and away from the contents of Castiel's stomach.

"I thought your hands were behind you," Castiel commented as Dean leaned him against the wall. Rather inelegantly Castiel slid to the bottom of the wall releasing a sigh once he was off of his feet. His head still seemed to be stuff with cotton, and his eyelids felt heavier than usual.

"You get to be in my occupation with my record, you learn a few things," Dean responded before settling himself beside Castiel.

"Yes, your occupation," Castiel muttered with little energy, his gaze drifting aimlessly around the all too familiar room, "apparently in your occupation you not only break the law but break logic." The former sailor brought his gaze back onto Dean, who shifted uncomfortably at the sudden intense gaze that was focused onto him.

"What was that creature?" Castiel growled, although his question was not as intimidating as he had hoped, thanks to his current condition.

_I don't care about my condition,_ he thought, _I just want answers_.

* * *

Gabriel's eyes were focused on the beautiful town before him, almost faintly he could make out the sound of roaring water that fell from the back.

"Drop the anchor!" He heard the commanding voice of Zachariah order from behind him, while the elder brother remained station at the very front of the ship. Disappointed at the lack of the ship that was as dark as the night, Gabriel knew that the only reason for them to stop here would be for resupplying before they continued to try and find the vessel that his younger sibling remained on.

Once the boat was at the pier, Gabriel waited for the mass of sailors to get off the ship before he too made his way off of the Vessel, his eyes glancing around the other people that were currently on the pier.

Following the rest of the royal officers, Gabriel made his way into the town. He could almost admire the tropical beauty and design that was Sioux Falls, but the image of a pair of striking blue eyes and a mess of dark brown hair tugged at his usually joyful energy.

It was when Gabriel felt the hairs on the back of his neck rise that he felt like a pair of eyes were constantly focused on him. At first he tried to shake off the feeling, but it remained no matter how much he tried to shove the thought down. Suspicion beginning to take over, Gabriel began to weave through smaller streets and alleyways; trying to lose the pair of eyes that seemed to follow him everywhere. Rushing, Gabriel ducked into an alleyway, and he rested against the rough wood that formed one of the sides of the building he leaned against.

A hand muffled the shout he tried to give as it covered his mouth, and his gaze locked onto a pair of blue eyes that stood above him. The stranger's arm held Gabriel against the wall, pressing him into the wooden boards.

"We need to talk," a familiar voice with a certain accent whispered, and Gabriel's eyes were wide with surprise as recognition flooded inside of him. Slowly the hand pulled away from Gabriel's mouth, along with the arm. The taller of the two stood a few inches away, arms crossed while his eyes remained slightly narrowed. A similar look was on Gabriel's face, a frown set on his forehead while he leaned against the wall.

"You again?" Gabriel questioned, an eyebrow arched as he crossed his legs. The pirate gave a small smirk, though the rest of his face remained serious.

"Yes, yes I know. Splendid time we spent together, I miss it too. Anyways-"

"Where's my brother?" Gabriel intervened, he wasn't in the mood to tolerate the sarcasm which seemed to come to the pirate like breathing as he spoke. He watched as the pirate's eyes narrowed, a scowl carved into his face.

"That's the thing, our captain and ship have been," the pirate paused as he tried to think of the right description of the matter, "compromised."

"Would you like to be a little bit more in-depth, or do you expect me to infer from that empty response?"

"Look," the pirate snarled unexpectedly, his face a mask full of anger and annoyance. "I nor you have the time to dance around such witty rubbish that we try to come up with. I'm saying that the Impala and our captain, along with your dear little brother, have been captured."

Gabriel froze, his heart seemed to skip a beat as the words left the foreign pirate's mouth. Immediately doubt began to fill his pause, it was impossible for such a thing to happen.

"How could I trust you, after everything?"

"Because it's not just your brother's ass that's in trouble now. It may have seemed bad when you guys were taken aboard while we were in charge, but if the pirates who stole the Impala are who I believe them to be then we have a major life-death situation on our hands."

"Why wouldn't it have been a life-death situation before? You're pirates, breaking the law and screwing the natural order and ideals is all that you seem to do!"

The pirate raised an eyebrow, although his eyes almost transitioned into what seemed to be a playful look; but he caught himself and remained serious.

"I find it rude that you would think all of us to be the same." At the sight of Gabriel's threatening eyes, the pirate sighed and shook his head.

"I can assure you that Dean Winchester would never have killed you or your younger brother."

"Why wouldn't he?"

There was a slight pause, the pirate seemed to want to refrain from giving away too much about the infamous pirate captain.

"Both of you were interesting. Honestly he was just amused by your brother's constant attempts at capturing him. The two were quite a curious case on the ship." Gabriel's brow furrowed, his curiosity was screaming at him now as word of his younger brother was carried from the mouth of the pirate and to the ears of the head of the guard.

"How do you mean?" A smile passed onto the pirate's face.

"Your little brother somehow managed to break out of the brig each day for ten days until we came here. Always managed to get out a different way. But he never could make it out thanks to Winchester. To be plain, I almost want to say that it was fun for both of them, despite the predicament that your brother was in. Although I know the captain was probably enjoying it a great more deal, hell we started keeping a record to count out the wins and losses."

Gabriel's eyes were tinged with pride, causing his eyes to shine as he heard of how his brother kept fighting. But he had to focus, because Gabriel knew that it wasn't good enough now that Castiel seemed to be caught in an even greater predicament.

"I believe you," he assured the pirate, who seemed to relax at the sound of Gabriel reassuring that he spoke of the truth; his shoulders dropping while his whole face softened ever so slightly.

"Well then you don't have time to waste. If the pirates who took away the Impala are who I believe them to be, then both of the people we care about are most likely in a quite dire situation. You should find that the Impala while most likely be sailing to the Nipoditier islands, and hopefully your dear little Cassie along with my captain should be on that ship."

"The Nipoditier islands, are you positive? That's not exactly-"

"I'm out of options at the moment, so when I Nipoditier islands, I mean that I would bet my second cousin's life that that is precisely where that ship is headed." Gabriel nodded, deep down bubbling with excitement at getting a lead on where his brother could be. He reached out a hand towards the pirate.

"Thank you," he uttered, watching as slowly the pirate peeled his own hand from his crossed arms and shook Gabriel's own. Gabriel's face grew stern though and he clenched tighter onto the pirate's hand.

"If my brother is hurt or you have been lying to me, I will hunt you down."

Once the pirate's eyes grew serious Gabriel knew it was unlikely that this man was lying, but he felt the need to make the threat. His face softened, and he spoke with no threatening tone in his voice as he continued.

"As for Dean Winchester, I can't assure you of any promises of not being placed into custody; I'm afraid that boy has quite a record."

Gabriel watched as the pirate's eyes suddenly filled with mischief, a certain spark glowing inside them.

"Why don't you let me worry about Dean later, for now I just need you to find them before our fears could become a reality."

With a smile the pirate turned and rushed away through the alleyway, disappearing around the corner before Gabriel even had the chance to give chase. Sighing, Gabriel tried to go over all that the pirate had told him; he closed his eyes in concentration while his fingertips found his temples.

"Nipoditier islands," he muttered before facing opposite of the direction in which the pirate had headed, his eyes skimming over the bustling street. Heart racing with excitement, Gabriel rushed out of the narrow alleyway and back into the street which crowded with both noises and people alike.

Making his way to the pier, Gabriel raced across the wooden boards and up the ramp. Golden eyes scanned the deck quickly before he made his way over to the captain's quarters at the lacking presence of a particular man with cold eyes.

One hand curled around the doorknob while with the other Gabriel knocked on the door; his repetition matching the beat of his quivering heart.

"Come in," a familiar voice called out, and hurriedly Gabriel's hand twisted the brass knob and shoved the door open. He watched as curious blue eyes scanned across his breathless form.

"What is it?" Zachariah asked, trying to search for a clue or hint as to why Gabriel came to him with a lack of breath.

"I have a heading."

* * *

Dean faltered for a second, feeling the cracks spreading teasingly along the steel trap in his mind. His eyes found themselves glancing away from Castiel's, instead they admired the dark wooden boards that the two sat down on.

"Dean," the former sailor growled weakly, and Dean closed his eyes.

The last thing he wanted to do was walk down that hall, to admire the dark art gallery which hid the pictures that hung on its shadowed walls. Pictures which he never wanted to take a second glance at. Pictures that he wish he could gather up and bring them to light as they burned with a great fire that roared. Pictures, that he knew would break him.

Because they broke him when he had painted them.

"Dean," he heard a rough voice calling out to him, nudging him away from the hallway and back to shades of blue which stared at him with a great intensity. Why should he turn on the lights for this stranger, this man?

_Because you threw him into this mess_, his own voice responded inside him, _he deserves to at least know about them. To know of the wolves in which you threw him and yourself to._

Dean nodded absently, his gaze having drifted away from Castiel's before he released a sigh. Sitting up, Dean brought himself to stare at the former sailor. Staring back with heavy eyelids, the question was blatant in his eyes while he waited expectantly.

"Cas," Dean managed to choke out before clearing his throat. He paused, taking a deep breath to try and calm his rapid heartbeat.

"Do you remember our first conversation, after you locked yourself in the supply room, and right after Gabriel escaped?" Dean watched as Castiel's eyes searched to recall the conversation that he spoke of. Recognition then flared in Castiel's eyes, and he nodded; though his face expressed confusion.

"How about the Hellhound, you remember that?" Castiel frowned, and Dean knew that he was having trouble recollecting everything, the cause being the concussion that the former sailor had received. His eyes seemed tired, and Dean almost wanted the former sailor to fall unconscious so he wouldn't have to continue speaking.

But the former sailor shook his head, and Dean admired the way he was trying to raise himself from the claws of the inevitable slumber that he awaited him.

"I would appreciate it, Winchester, if you could perhaps enlighten me of the information you had shared with me that night which was eleven days previous to this one."

Once Castiel had finished speaking, Dean was quickly drawn out of his shadows and couldn't help but give a small laugh. He watched as Castiel's eyes narrowed, although instead of coming off as annoyed the former sailor rather reminded Dean of a cat; this caused the pirate to only laugh a bit louder. After noting the displeasure that spread all over Castiel's face, Dean tried to calm himself while a smile was drawn from his lips.

"Even with a head injury you still manage to keep up the vocabulary," Dean chuckled, "Castiel Novak, you are a man like no other which I have met; and I've been around." His eyes were drawn to the man's mouth as the top of Castiel's lip began to pull up to join him in a smile. But the former sailor resisted, and instead responded with a shake of his head.

"Dean, could you please remain focused onto the topic at hand before I end up unable to hear such words that I am waiting for because I will be too busy sleeping when I would rather be awake?"

Forcing himself to hold down the smile that was trying to mold his lips, instead Dean nodded and inhaled deeply.

**Because I am so swell, you'll have to wait till the next chapter to hear of Dean Winchester's possible confessions! And the return of Gabriel and a certain pirate with a lovely accent, I assure you it isn't the last we've seen of either of the two! Please review, favorite or follow if you enjoy! Seeing everybody's reviews and the like always bring a smile to my face; thank you guys so much!**


	15. Leaking Memories

**And We Are Back! I'm so sorry for the longer-than-usual wait everybody, but I decided to take a break from writing and remember what the outside world looked like. Now that I remember what nature's like, I'm ready to get back to the computer and continue writing! Thanks to DeerTopus C. VonZenHousen(can you now? and thank you, I love writing his dialogue :3), Air Guitar Pixie(Ah, but waiting builds up the suspense, no? As for tragic backstory…..And as for Gabriel, I guess you'll have to see what I have in store for him, as well as Balthazar!), mywarisalreadywon(It's no problem at all, I just appreciate you reading my story in the first place ^_^ as for Sammy, well we don't want to give out too many spoilers), Dancerline(Balthazar and Dean are bros, I'm sure we haven't seen the last of Balthazar coming to save our favorite damsel in distress ;) And what would make a story without its cliffhangers, I'll apologize only for the longer wait!), and Akayuki Sawada( I apologize for giving you a headache! But thanks once more for pointing that out!) for reviewing! A thanks as well to those who have followed and favorited, all of you are amazing!**

* * *

_"Even with a head injury you still manage to keep up the vocabulary," Dean chuckled, "Castiel Novak, you are a man like no other which I have met; and I've been around." His eyes were drawn to the man's mouth as the top of Castiel's lip began to pull up to join him in a smile. But the former sailor resisted, and instead responded with a shake of his head._

_"Dean, could you please remain focused onto the topic at hand before I end up unable to hear such words that I am waiting for because I will be too busy sleeping when I would rather be awake?"_

_Forcing himself to hold down the smile that was trying to mold his lips, instead Dean nodded and inhaled deeply._

* * *

"The _Hellhound_, is the name of a ship that's used in children's stories; it hasn't been around too long but it's pretty well-known. You with me so far?" Castiel gave a small nod, black spots beginning to speckle his vision. He tried to focus on Dean's face, to cling onto the words that spilled from the pirate's mouth.

"And the story goes that the Hellhound is a ship of chaos; yet somehow it remains pure, a cold and unclean purity. Of course, who else would captain a ship of such darkness as the king of oblivion himself. Lucifer, Satan, Beelzebub, the Morning Star, the Devil. As many titles as he has received, he is still just as ruthless, dark, and twisted," Dean paused and Castiel realized that his face had proceeded to grow a look of confusion after hearing such spite in the pirate's words.

"At least that's how I interpreted it from the stories," the pirate said with speed that Castiel did not trust. Yet the familiar look was in Dean's eyes as he shared, and Castiel resisted from releasing a huge outburst; he couldn't scare Dean off now that the pirate was sharing.

"Anyways," he continued. Dean's words came slowly, from both trying to make sure Castiel heard him despite his focus gradually dwindling away, and by the looks of it he was trying to figure out what he should share with Castiel.

"Since you must be educated, I would presume you would know of the creatures that Lucifer created to serve under him?" Castiel looked away from the pirate and closed his eyes, searching his brain with the answer that was taunting him while it remained unreachable. With a mighty leap Castiel latched onto the answer to Dean's question, and once he did his eyes burst open wide. Slowly Castiel turned his head and faced the pirate, who held a grim expression.

"You are not suggesting that a creature such as that actually exists in this universe, are you?" Castiel scoffed, yet just at the motion his head throbbed and he closed his eyes tight. Opening them again, he saw that Dean's face remained both unhumourous and genuine.

"That's exactly what I am suggesting pretty boy," Dean replied, his eyes unwavering as they remained on Castiel's. At first Castiel narrowed his eyes ever so slightly once Dean used the familiar suggestive nickname that he bestowed on the former sailor without his consent.

"So you're telling me that demons exist in our world?" Castiel was filled with skepticism at the impossible possibility.

"How else would you like to explain those lovely black eyes of hers?"

"Trick of the light?" But as soon as those words left his mouth, Castiel knew that such a theory wasn't correct.

Dean shook his head, a meager, sad smile planted on his face. "We both know that light wouldn't affect a person's eyes like that. Hate to be the one to let you know that black-eyed bitches are the real deal buddy."

Castiel's eyes grew wide, he found his heart beating at an unusual fast pace again as it raced inside his chest. He was mentally swamped with the memories of those dark, soulless eyes staring into his own. Black eyes seemed to overwhelm him, and soon they began to obscure Castiel's own vision as he felt his eyes withdrawing behind the curtain of skin.

"Cas?" Faintly Castiel heard the voice of the former sailor, but the only thing on his mind was the familiar feeling of falling into the murky unconscious.

"You have to stop doing this when I'm getting serious, man." Dean muttered as he leaned closer to Castiel. Once Dean had confirmed about the wretched creature above deck, he was surprised at how the former sailor reacted.

Tensely, Dean watched as Castiel's eyelids began to shut down after his eyes had widened to a ridiculous width. The fear and shock in the sharp blue eyes almost drained Dean, he had been unsure of how the news was to be taken by such a serious character that was Castiel Novak.

But once the man's eyelids began to close, covering those blue eyes, Dean's worry expanded inside of him.

Without hesitation the pirate had called out to Castiel, trying to see if he was still conscious. After repeatedly voicing Castiel's name several times and was only met with nothing but silence, he found that his own heart's pace began to hurry.

Dean placed himself in front of the now unconscious sailor, whose skin no longer retained its tanned color and now was in the form of a sickly paleness.

"Cas?" Dean tried, his face closer to the man in front of him as he raised his voice. Bringing his locked hands up Dean lightly slapped Castiel's cheek, trying to get a reaction out of the man; to draw him back to the waking world.

"You are one heavy sleeper," he joked; although it wasn't as fun when there was no one to look at him disapprovingly. Or, using Castiel's perspective, a mix between both disproving and confusion.

Shaking his head, Dean cast his eyes around the cell to seek out anything that would cause a spurt of genius.

If he really wanted to he could hit the former sailor harder, but the more plausible idea that the former sailor could have a concussion caused Dean to hesitate. The last thing he wanted to do was worsen the man's already poor condition.

Dean's eyes rested upon the unpleasing sight of the contents of Castiel's stomach that sat in the far corner. His nose wrinkled at the growing stench that was just beginning to fill the room. A bad move on the former sailor's part, but then again Dean had reacted just about the same after his own encounter with Meg; save for the contents of his stomach exiting his body.

Yet at the smell of the disgusting bile, the spurt of genius that Dean had been searching for struck him in the face.

Turning his attention back onto the pirate that was sprawled out in front of him, Dean quickly sat down and began to unlace one of the two black boots that he wore. Removing the footwear, slowly Dean sniffed the boot himself, and he quickly recoiled with a sour face.

As he held the boot, Dean froze as his gaze shifted between the black shoe and the unconscious former sailor. Did he really want to wake him up?

_He's going to have a lot more questions now, not to mention a serious head injury,_ a part of him argued.

_It won't hurt if I try the whole smelling salts thing, we don't even know if the boot will work_, he countered. Although once the thoughts had been thought the stench of his black boot wafted up to his nostrils, and Dean quickly stretched his arms away along with the unpleasant smell.

"Damn," Dean muttered before bringing his focus back onto the slumbering form of Castiel. The former sailor's chest rose evenly with each breath, up and down. It was almost peaceful, besides the dried blood on his head and the fact that Castiel's hands were secured behind him.

But suddenly it wasn't so peaceful, and Dean's eyes grew wide as he felt part of the steel trap in his head crack open unexpectedly. He could feel the images leaking out, and it affected everything it touched. With a smoky tendril the leaking memories reached out and destroyed the real world.

Suddenly the room was suffocating, and Dean could hear the screams serenading him. He could feel the twisted feelings bubbling inside of him as he looked into eyes that were filled with fear. A sadistic smile that he recognized as his own only terrified him more. His heart was slamming against his chest with each heartbeat. Chills only raced further down his spine as he could pick up the sound of laughter. Cold. Heartless. Laughter.

"No!" Dean shouted, his hands now pressed tightly against his ears while he ignored the cold chain that pressed against his face.

With frightened eyes the pirate looked for something to hold onto, anything to clog the leak. His gaze latched onto Castiel's sleeping form, and Dean acted quickly. He released his ears and picked up the foul boot.

Reaching forward, Dean thrusted the boot under the former sailor's nose, his eyes screwed shut as he tried to block out the hideous images that continued to soil the difference between reality and the pollution inside of him.

* * *

_"How disappointing, Castiel."_

_Thump._

_"I expect better from you, Castiel."_

_Thump._

_"You're a Novak,"_

_Thump._

_"And no Novak,"_

_Thump._

_"Will be a disgrace."_

_Thump._

_"You should be thankful that I'm only discharging you. Be thankful, Castiel."_

Castiel's eyes fluttered open, immediately meeting with a pair of petrified green eyes that drew him away from his dream. They were as wide as his own, but quickly his eyes flicked down to the reeking boot that was placed under his nose.

With a wrinkled nose the former sailor tried to shy away from the horrendous footwear, and appreciated its absence when Dean quickly brought the boot back to its proper place on the pirate's foot.

"That was unpleasant," Castiel muttered as he tried to breath in air that wasn't polluted with the stench of Dean's feet. Shifting, Castiel tried to sit up more as he remained against the wooden boards.

Focusing back onto Dean, he noticed how the pirate's eyes were still bright with panic. With shaky breaths the pirate tried to calm himself, though Castiel easily noticed how tense Dean remained.

"Sorry, but I was kind of low on ideas," forced humor was evident in Dean's voice, and Castiel's eyes narrowed in faint curiosity.

"What's wrong?" Castiel asked bluntly, it was obvious that the pirate hadn't been that worried about him, he had only fallen asleep.

Observing attentively, he marveled at how strange Dean was acting. Sure the circumstances were now a bit... different, but Dean had already held knowledge about whoever was above them. And Castiel had always felt that the pirate was strange, but now he was acting different.

As soon as Dean heard Castiel's question, his eyes locked onto Castiel's. The former sailor narrowed his eyes slightly as he felt his heartbeat speed up slightly, deciding to ignore it. Silence began to expand between the two, and Castiel watched as the emotions in Dean's eyes change.

At first they maintained their startled, frightened look. But then gradually it shifted to an eerie calm, like the silence followed after a threatening storm. Finally those green eyes rested onto the most vexing, familiar look that Castiel was growing to hate. They were guarded, dark and hidden; unwilling to give nothing to those who beheld them.

But once the look was settled onto Dean's face, he surprised the former sailor when his face seemed to soften slightly. Something that would be near impossible to notice to others, but Castiel caught the change as soon as it happened.

Puzzled, Castiel continued to stare at Dean as both waited for a reply and tried to ignore his screaming subconscious; which beckoned for him to rest his eyes once more. Instead he bore his eyes into the varying shades of green that occupied Dean's.

"It's nothing," came the final reply before Dean turned his head and began to retie his boot. "How's your head?"

Castiel was almost unsettled by the way Dean was acting. It was too quiet, too guarded. He resisted the urge to ignore the question completely and interrogate Dean, although he wanted to deeply.

"I've got a concussion, usually not the most pleasant condition to be in." At first Dean froze, and suddenly the Dean Winchester that Castiel was more familiar with burst forth with a great laugh.

"Sarcasm now? I didn't think you understood how to use such wit." The previous feelings of unsettlement gradually escaped Castiel. At the sight of Dean's eyes now lit up like a child. There was no sign of his former mood; the transformation impressed Castiel.

"I am human, Dean. Despite my different use of my vocabulary compared to others, I do understand the concept of humor." Castiel's response was only met with the sound of laughter, and Castiel couldn't help but smile slightly as well.

Dean's laughter immediately froze as his eyes had caught sight of Castiel's smile, and the pirate leaned forward. His face was only inches away from Castiel's own, and Castiel held his breath to see what Dean was up to now.

"Did my eyes deceive me or did I just see you smile Cas?"

Embarrassment flooded into Castiel as he felt the heat going to his cheeks without his control. He turned his head away from the pirate, trying to hide the redness that was spreading over his face like a disease.

"If it's alright with you, Winchester, I'd like it if you could contain your humor and return to the serious situation we have at hand."

Out of the corner of his eye he watched as Dean seemed to give a mock pout, before the pirate returned to sitting across from him. Slowly, Castiel faced Dean again, and he was glad to see that Dean still held a brightness in his eyes along with a smile that tugged at his lips. The last thing he wanted to see was the dark, guarded look that had masked the pirate's face.

For now he could be satisfied, for now he could live without delving into a past that no one else should see.

* * *

**Sorry this is shorter than usual, but I really like the way that it ended there. Also, if I had continued it would have been a little bit too long than I like to keep my chapters at. Rest assured the rest of the chapters will be the usual length. Thank you for reading and please review, favorite, or follow if you enjoyed! See you for the next installment!**


	16. Diverse Disputes

**New Chapter! I apologize very much for the strange code that happened on the previous chapter, it's fixed now if you haven't read it yet. For all of you who reviewed and notified me about that issue, thank you very much! Thanks you DeerTopus C. VonZenHousen(I hope this story will be long too, it depends on how I write out the outline I came up with, how long it takes for a certain point to be covered. But I hope for many chapters as well), Kather-Swine(Thank you X3), and Akayuki Novak(Those Winchesters, not very good about sharing is caring, eh? Then again, there may be more at hand here than just typical Winchester behavior….) for reviewing! A thanks as well to my new followers and favoriters, welcome to the crew! Let us move onto the next installment, shall we?**

* * *

_Dean's laughter immediately froze as his eyes had caught sight of Castiel's smile, and the pirate leaned forward. His face was only inches away from Castiel's own, and Castiel held his breath to see what Dean was up to now._

_ "Did my eyes deceive me or did I just see you smile Cas?" _

_ Embarrassment flooded into Castiel as he felt the heat going to his cheeks without his control. He turned his head away from the pirate, trying to hide the redness that was spreading over his face like a disease._

"_If it's alright with you, Winchester, I'd like it if you could contain your humor and return to the serious situation we have at hand." _

_Out of the corner of his eye he watched as Dean seemed to give a mock pout, before the pirate returned to sitting across from him. Slowly, Castiel faced Dean again, and he was glad to see that Dean still held a brightness in his eyes along with a smile that tugged at his lips. The last thing he wanted to see was the dark, guarded look that had masked the pirate's face. _

_For now he could be satisfied, for now he could live without delving into a past that no one else should see._

* * *

"Demons walk the earth," Dean nodded after Castiel tried to start the conversation.

He was still shaken on the inside, but he did his best to mask it in front of the former sailor. Gratitude skimmed the top of him, he was lucky that Castiel was able to pull him away from the polluted area, despite the former sailor being unaware that he had done so.

Nonetheless, Dean was thankful.

"Yeah," Dean paused as he tried to think of how to continue. Releasing a large breath, Dean shook his head. "I kind of don't know where to go with that. What else do you want to know?" He brought his head up to watch Castiel's eyes, it was easy to see that the former sailor was racking the inside of his brain to list out all of his questions.

_I wouldn't be surprised if the man's making a frickin' list from most important to least important. Oh God, what if he organizes it alphabetically too?_

"Can they be killed?" Dean was drawn away from his distracting thoughts as Castiel began his interrogation.

"I have yet to see if they can," Dean replied with a sour face, and he squeezed the back of his neck. He noticed how Castiel frowned at the news, his eyes calculating.

He felt a mass swirling in his gut; Dean was able to recognize it as admiration. Here was a man who just learned of dark creatures and he's already trying to find a way to win, to break free.

_Although he has yet to succeed in that category_, the corner of Dean's mouth twitched up as he thought of his previous game with the former sailor. Castiel seemed to notice his small smirk though, and his eyes narrowed further than usual. Possibly through the look in Dean's eyes Castiel seemed to understand what Dean was thinking about, and his lips formed a tight, straight line while his eyes remained narrowed.

"Just because I was unable to get past you doesn't mean that I'm weak," he warned with frustration evident in his eyes. Dean shrugged, but after hearing Castiel's words mischief blossomed in his eyes.

"So you admit that I won our game?" He joked with a raised eyebrow, and he watched as the fire in Castiel's eyes blazed even brighter, roaring with irritation. He kept his eyes locked onto Dean's as he responded coolly.

"If you could remain serious for just a moment, if you could take the time to break away from your usual careless attitude for just a few seconds, maybe, just _maybe_, it could be possible for us to get out of this mess that you've caused in the first place!"

Surprise raced through Dean as he listened to Castiel. This was all _his_ fault?

"Pardon you, _pretty boy_, but I did no such thing!" Dean all but snarled at the former sailor, his own eyes alight now with annoyance.

"Stop calling me that, damnit! I don't understand why you feel the need to call me such a thing, the only reason I can think of is that it's probably because of that paper skull of yours!" Castiel shouted back.

"You say I have a paper skull and you still have yet to best me!" Dean countered.

"You chose brawn over brains you ignorant mud," Castiel replied with hanging eyelids and a voice full of contempt.

"Well if you represent brains then obviously brawn is more victorious!" Dean snarled. Both were seething with irritated rage at one another, their looks vicious and vexing.

"How the hell does an excuse for a man like yourself end up being the captain of a ship. Who the hell would want to follow you?"

"I like to think it's my perky nipples that attract the people," Dean replied without losing a beat, his eyes now split between the glow of sarcasm, and the fire of rage. His face dropped his typical smirk though as he grew serious once more.

"You know nothing about me, Castiel. You've never faced this threat before, you don't know what stands between us."

* * *

Castiel paused, holding back his arsenal of retorts once he heard the emotion in Dean's voice once he had spoken. There was no more rage, no more annoyance after his words had left his mouth.

Instead what had carried over to him was more somber, no trace of humor whatsoever. It was sad, and the look in his eyes was no longer a burning flame; now it was dim and only flickered like a candle that was about to be extinguished.

Immediately Castiel came to a conclusion, and he felt his anger seep away as confusion and surprise filled its place.

"You're afraid," his voice was low as it came out soft as a whisper. Dean drew his eyes away from Castiel and cast them down. Castiel followed his gaze and watched as the pirate fumbled with his hands.

Suddenly Dean looked up, his eyes low and dangerous. For once, Castiel himself was fearful of the pirate, he felt a shiver run up his spine as his eyes looked into Dean's own. The green eyes were almost fire itself, not a trace of the previous gaze that the fire now relieved.

"You think I'm afraid?" Dean growled, and Castiel froze at the sound of his voice. It mirrored the emotion in his eyes, low and dangerous. "I am anything but afraid, Castiel. Those _things_ up there may look human, but they are anything but. They are vicious, cold, and void of all emotion except for the joy they get from the pain they create. Fear won't due either of us any good."

Castiel's words were silent as he stared at Dean Winchester. As soon as he finished, the pirate seemed to deflate. Energy sucked out of him and all that was left was a shell, filled with secrets that Castiel wanted, _needed_ to know.

Why does Dean know of these creatures when it seemed the rest of the world was oblivious? What is he hiding from those he deemed most loyal, and yet teases that which he hides in front of a man whom he knows almost nothing about?

"Dean," Castiel started, his voice slow and quiet. "How do you know about these demons?"

Immediately Dean tried to dodge "I've been-"

"Dean."

"I didn't ask to share my life story with you Cas!" Dean shouted, fire and pain burning in his eyes, twisting and fighting.

Castiel felt more words being shoved up his throat, but he held them back. Closing his eyes to escape the fires that raged in a forest of green, the former sailor took a deep breath and calmed his screaming curiosity.

Doing what he usually did for the sake of clarity, Castiel began to organize his thoughts.

_Stupid, stupid! Everything was all fine until you accused him. Although it did carry an interesting reaction. Obviously he has history with these demons, or that Meg one at least. _At the mention of Meg Castiel gave an inward shudder.

_Focus on getting out, then if we both get out of this predicament you can interrogate him. Better yet, you could finally get off this horrid vessel of black._

Castiel's ears perked up at the sound of Dean clearing in his throat, and the former sailor opened his eyes. Dean's own lost their glow of ferocity, now they seemed to shimmer with an almost apologetic, regretful sheen. He remained silent as he watched Dean rub the back of his neck again, noting that it seemed to be a subconscious habit for the pirate.

"That may have gotten a bit too intense for both of us," Dean admitted with a small smile before dropping his hands back into his lap, "we cool?"

Castiel frowned slightly, amazed at how quickly the pirate seemed to recuperate from his dangerous mood.

"I've mentioned this before and I'll mention it again Winchester, you are certainly different."

At first, Dean pursed his lips and Castiel managed to catch sight of the guarded look on the pirate, but he almost sighed in relief as a familiar mischievous glow danced in Dean's eyes again; leaving no trace of the darkness that the pirate typically withheld.

"Does that make me special?" Dean recited with a smirk, both he and Castiel instantly remembering the conversation the words they spoke with came from. "Anyways Cas, bottom line here: You're injured, and on top of that we're trapped down here while a bunch of disgusting _demons_ are sailing this ship. Probably the only reason we're alive right now is because of Meg."

Castiel's head tipped to his right as he thought about Dean's explanation. "How were they able to apprehend the ship, Winchester?" Observantly Castiel watched as Dean frowned slightly.

"I was hoping there wouldn't be any trouble, so I only left a small handful of my crew on the ship. They were easily overpowered, not much of a surprise there."

Confusion began to settle into Castiel, who brought his head back up. "If you only had the crew members on board, and you were in the town, how'd you end up on the ship without the rest of your crew?"

A smile toyed on Dean's face, and Castiel almost thought that it seemed like a bit of color was going to the pirate's face.

"Yeah, well thanks to Balthazar we got to the port just as my ship was pulling out." Words were about to leave the pirate's mouth, but then Dean sealed his lips as he paused. Castiel couldn't help but notice how Dean seemed..._flustered_.

"You didn't get on the ship, perhaps, because I was still onboard; did you?" Castiel found himself perplexed at the notion. Surely Dean wouldn't have come to his aid, not when demons were onboard? Yet here the pirate was, sitting across from him with a face that seemed redder than normal.

Dean laughed, although it wasn't the usual, full laughter that the pirate usually expelled. This one seemed more forced, Castiel squinted as he stared at Dean quizzically.

"That's cute," Dean scoffed, "sorry pretty boy but I wasn't just going to let them take my ship." Dean paused before shaking his head, "although that still kind of happened. But yeah, totally not for you. Almost forgot you were on the ship!" He repeated his strange laughter once more, leaving Castiel even more confused than earlier.

"If you say so," he replied, still unsure of Dean's true intentions as to why he boarded his stolen ship. "Wouldn't it have been easier for you to get your ship back by-"

"It doesn't matter Cas," Dean quickly interrupted, and Castiel was still stumped as to why there appeared to be such redness gathering in the pirate's face. "Besides, you need to stop getting so off topic man, it's not exactly helping the situation."

Castiel snorted, _he_ was the one getting off topic?

Dean seemed to interpret his thoughts, "Yeah, you get off topic. A lot."

Frowning, Castiel began to bring up that Dean has been off topic before as well, but the pirate quickly intervened his words. "You're doing it again."

A defensive noise escaped Castiel's mouth before he grudgingly closed it, annoyance brought on by the victorious look that was formed from Dean's face.

"Then what do you suggest we do, Winchester?" With a raised eyebrow, the former sailor awaited to see what could leave the pirate's mouth that would even remotely resemble an escape plan.

* * *

Dean looked up in thought, eyes mindlessly looking at the dark boards of _his_ ship. He bit the bottom of his lip, considering two options that were the most obvious.

They could probably get out of the brig, maybe manage to grab a lifeboat but that was unlikely. Sadly, none of the demon pirates that belonged to Meg's crew would require sleep, so the black-eyed creatures could maintain a decent amount of personnel on deck.

The second option was the one that Dean didn't want to contemplate, though it struck various chords.

"There's a reason Meg kept us alive," Dean thought aloud. He looked away from the ceiling and back towards his injured companion. "Thoughts, pretty boy?" The narrowed eyes that he was met with brought a smile to his face, Dean couldn't help making a bit of fun despite the situation. It was a defense mechanism, a way to avoid his other side.

"I thought we already established that your little nickname is greatly unappreciated and not humorous in any aspect whatsoever."

"You're getting off-topic again, Cas," Dean continued with a broader grin, and he watched as Castiel grit his teeth in annoyance.

"Well obviously you have a history with her," Dean immediately felt the crack in the steel trap poke at its bindings, somehow the pirate was able to hold it back for now. "Of course no need to get into that topic at the moment," Castiel added in hurriedly. Still frowning, Dean nodded while he glanced around the cell.

_At the moment,_ Dean bit the bottom of his lip again as he recited the former sailor's words in his head.

"Meg's never really been the sentimental type," he mentioned before he felt the crack poke again at its restraints. Dean couldn't help but wince, his eyes scrunching up as he shook his head. "Not many reasons as to why she'd keep us alive," growling slightly Dean rubbed his face, "Meg wouldn't do that, or the other possibilities. She's not too keen on breaking his rules, but what else is there?"

"His rules?" A rough voice pushed through his rambling and Dean glanced at Castiel.

"Head honcho," Dean explained. He watched as it clicked in the former sailor's head and Castiel paled slightly while his eyes grew to an alarming width. "You're not gonna throw up or pass out again, are you?"

"Give me a moment," Castiel replied as he tried to readjust how he sat. Watching, Dean waited until Castiel seemed a bit less panicked. Surprisingly Castiel was handling it rather well, "Didn't believe in Satan, eh?"

"I'm more into the belief of facts, things I see with my own eyes. As for Satan, I didn't believe that he would be the captain of a ship that sails around; that was a children's tale!"

Nodding, Dean sighed and got up. Treading lightly, the pirate walked up to the bars of their cell and rested his head against them.

"Here I am, the great Dean Winchester locked in his own brig," he muttered before turning around to face Castiel.

"Dean," the former sailor spoke softly as he looked up at the pirate with round eyes, "What do you propose that we do? You know more of these demons, if I got us out of here, could we take them on?"

Sadness glossed over Dean's eyes as he tried to figure out what course of action he wanted to take.

"Few things can harm a demon," he began with distant eyes, "iron and salt sting but they won't kill."

"Salt?" Castiel repeated with confusion beginning to twirl in his irises. "If the ocean's made of salt water, why are they sailing? Surely we could use that to our advantage?"

Regretfully Dean shook his head, "for some reason it doesn't affect them. It may have to do with the quantity or quality of salt, I don't know." He shrugged as he looked at Castiel. The former sailor's response was a simple frown, a trait that Castiel seemed to carry around constantly.

Sighing, Dean shook his head, "I just don't know if this is a battle we could handle. I can only see us getting out with a lifeboat and a crap ton of salt. You having that injury only hinders that further, so yeah. The odds are just never in our favor are they, Cas?"

"Seems that way," Castiel muttered, and Dean could imagine what the former sailor was referring to; it brought a small smile to the pirate's face.

Straightening up, Dean got up and walked back to where Castiel sat, dropping down next to him. Slowly he leaned back, his head hitting against the wooden boards. Silence expanded between the two, although Dean didn't find it awkward; in fact he almost found it comforting.

Closing his eyes, the pirate took a moment to listen to his ship and the ocean. Barely, he could make out the sounds of the crew members working above him.

"Well this is awesome," he muttered as he opened his eyes. Glancing over to his injured companion, Dean couldn't quite catch the former sailor's eyes. Sighing, Dean bumped his head against the wall again before making a decision.

Inhaling, the pirate fiddled with one of the buttons on his waistcoat. "Cas, I don't think you heard me the first time, but I'm sorry about all of this," using his hands to gesture about the entirety of the situation, "I didn't mean to drag you into this, it's my mess and you shouldn't have to be in the crossfire. So yeah, sorry man."

Releasing his fingers off of his buttons, Dean glanced over to the recipient of the apology. "Cas?" He asked tentatively, and then he leaned forward to catch the former sailor's eye.

It wasn't a gaze that he ended up meeting though, instead it was the sight of a sleeping Castiel; whose eyelids hid the blue eyes that Dean had been hoping to meet.

Huffing, Dean slumped back and leaned his head against the wall. "Seriously, again? Man you're timing is either terrible or perfect, I'm not quite sure." But his voice and face softened as he spoke again to a sleeping Castiel.

"I'm sorry, and I'm going to make sure you get out; I promise."

The only response Dean received about his promise was the former sailor's breathing, and he smiled at the sleeping figure before closing his own eyes.

* * *

Castiel cracked his right eye open slowly, relaxing once he saw that Dean's eyes were closed. He sat there for awhile in the silence, watching the calming rise and fall of the Winchester's chest as the pirate slipped into a quiet slumber.

"I don't get you, Dean Winchester." Castiel whispered with one last look at the pirate before he decided to close his own eyes. Unable to resist the exhaustion that had settled inside of him, he found himself drifting off into a darkness that he was well acquainted with.

**Hope you enjoyed! Sorry that these updates have been coming out a bit slower than normal, but I'm starting to get a bit busy out there in the real world. I may have to adjust how much I update come school time, but don't worry! Many, many chapters will follow! Please review, follow, or favorite if you enjoyed :D**


	17. Rise and Shine

**Welcome Back! Thanks to Akayuki Novak(He's a bit stubborn, that one..), cadlg7(Thank you so much! Glad you'll be joining along for the ride! Glad you like their relationship as much as I do), DeerTopus C.(Don't fret, I just believe that love is something that shouldn't be rushed; and I do have a reason for Meg kissing Cas, you'll probably get an answer in the near future), Kather-Swine(One does enjoy a sense of warmth to cuddle up to, no? ;), and Air Guitar Pixie(welcome back, and it's no good to tear your hair out! As for Castiel's little dream… that will be answered at some point in this story. As for Dean and Cas being alive, it's not quite as bad as it seems. Although who knows? I'm the author, for all you know I could make it seem worse or not as bad as it is/will be. Please don't make this story be the cause of your extreme hair loss ;) for reviewing! A thanks as well to those who have followed and favorited; we've just reached 32 followers! I'm glad to have all of you as my own crew ;) Now, no more of this long AN, onto the story!**

* * *

_Huffing, Dean slumped back and leaned his head against the wall. "Seriously, again? Man you're timing is either terrible or well-put, I'm not quite sure." But his voice and face softened as he spoke again to a sleeping Castiel._

"_I'm sorry, and I'm going to make sure you get out; I promise," after being only met with the former sailor's breathing, Dean closed his eyes._

* * *

_Castiel cracked his right eye open slowly, relaxing once he saw that Dean's eyes were closed. He sat there for awhile in the silence, watching the calming rise and fall of the Winchester's chest as the pirate slipped into a quiet slumber._

"_I don't get you," he whispered with one last look at the pirate before he decided to close his own eyes. Unable to resist the exhaustion that had settled inside of him, soon he found himself drifting off into his own peaceful slumber._

* * *

Gabriel stood at the bow, leaning against the smooth tan railing that ran along the perimeter of the ship. He couldn't decide whether he found looking out into the endless stretch of water peaceful or just plain bothersome. It was easy to understand to see why some found the ocean so daunting. Its vastness alone was what Gabriel found both beautiful and terrifying.

Somewhere out there in the vastness was his brother, and the longer he was out here in the ocean, unable to reach his brother, his worst fears began to torment him.

A hand rested on his shoulder, and he jumped at the touch. Turning around he was met with the familiar figure of Inias, who held a smile on his face.

"A bit jumpy today, are we?" He commented as he settled in next to Gabriel, both of them now looking out at the waves.

"It's not like I'm here with the best circumstances," Gabriel replied, frowning at the sky.

"I know, I'm really sorry about Castiel. But if I remember him correctly, most likely he's still alive. A bit too stubborn for death to take hold of him, aye?" Inias kept his eyes on Gabriel, concern for his friend obvious.

"Yeah that sounds about right." Gabriel answered with a small smile, the relief that Inias felt not going unnoticed. "Don't worry about me Inias, I'm just ready for us to hurry up and pick up my mess of a brother." Inias nodded thoughtfully, able to understand Gabriel's concern.

The older Novak brother had practically raised Castiel until he joined the navy. Gabriel hadn't been particularly pleased when his brother had decided to set his sights on the sea-faring occupation, but all the same he supported his younger brother. Although Castiel grew distant as he sailed, Gabriel would always think of the now strong and calculating man as the curious little child that he had been.

"Guess Zachariah isn't really searching out Castiel though," Inias pointed out. Both of the officers turned their heads and looked back towards the bridge. Standing at the helm was the captain, maintaining his air of authority as he shouted out commands.

"Fool's too focused on making himself look good. The man who captured the 'Great Dean Winchester'," Gabriel's voice laced thick with sarcasm, scorn also evident in the officer's words.

Inias glanced at Gabriel, "Dean Winchester; what's he like Gabriel?"

"Well it's not like I spent a great deal of quality time with him," the older Novak joked as he brought his attention back to the seemingly endless ocean. It seemed to stretch on for miles, the only thing that could be considered a border was where the sky and ocean met in the distance.

"He didn't kill us," Gabriel added, his eyes narrowing in thought.

"You say that like it's a bad thing," Inias jested, a constant smile still located on his face.

"Not necessarily, it's just pirates aren't always so…"

"Merciful?" Inias filled in, nodding in agreement. "You've got a point, doesn't seem like his usual style."

"Agreed." Gabriel replied, shaking his head before getting off of the railing and stretching his arms. "Now then, best we get to work. This little heart-felt talk was just wonderful, Inias."

"Always with the joking," Inias muttered with a slim smile as the two walked away.

* * *

Castiel felt himself gradually easing out of the soothing feeling of sleep. His head seemed to no longer be screaming at him, the waves of pain disbanded. He couldn't help but feel impressed that he had been able to stay conscious while he had talked and argued with Dean.

Eyelids slowly opening, Castiel blinked slowly several times as he tried to open his eyes, while the rest of him still felt a strong desire for sleep. After all, he felt warm and comfortable. Why was that? It's not like there was anything remotely close to cozy in the cell.

Lazily the former sailor finally opened his eyes, and noticed how his head was tilted. Looking up, Castiel realized that his head was resting on Dean's shoulder, the distance between the two a lot smaller compared to when they had fallen asleep.

Startled by the realization, Castiel immediately lifted his head, and realized too late that Dean's head had been resting on his. He watched as Dean jerked awake, eyes wide with alarm as he glanced around the cell.

"What's going on?" The pirate sleepily mumbled, confusion written all over his face. Castiel could feel the embarrassment inside of him, he fought desperately to keep the color from his own cheeks. Nevertheless, his whole face felt as if it was burning, he could only assume that it was an embarrassing shade of pink.

"Nothing's going on whatsoever," Castiel quickly replied, his heart racing while his stomach felt strange; he could only describe the feeling as if he 'had butterflies in his stomach'. Faintly, Castiel remembered some people using that strange phrase that seemed to describe what he was feeling at the moment.

"Uh," Dean grunted before the pirate closed his eyes again. Castiel couldn't help but roll his eyes, it seemed the pirate wasn't an early riser.

"Dean," Castiel began, deciding to try and keep the pirate from falling asleep again. The pirate lazily opened one eye, the green iris staring at Castiel with slight annoyance.

"Come on, Cas. Sleep good," Dean muttered before shutting a heavy eyelid over his open eye. Castiel frowned in annoyance, apparently Dean wasn't a good morning person.

"Besides," he mumbled, "what else is there to do?"

Frowning, Castiel stared at Dean to see if the pirate was kidding. But after nothing but breath coming from his lips, Castiel let out a huff of annoyance before he turned away from the captain.

Now that he was awake, Castiel began to feel the soreness that had been gathering in his arms. He glanced at Dean's hands, which laid in his lap. How'd the pirate get them in front of him?

Deciding to test himself, Castiel brought his feet under him, getting onto his knees. Exhaling, the former sailor unsteadily raised himself up all the way. He gave a small thanks to no one in particular that his head no longer seemed about ready to explode, or that his vision was no longer swimming with spots.

Thinking back, Castiel remembered that he had been sitting in the corner. Eyes flicking over to the corner, Castiel's nose wrinkled up at the unattractive contents of his stomach, the smell rather unpleasant in the room.

Coming up with a theory as to how Dean did it, Castiel rolled his head before he decided to start. Tensing up, the former sailor jumped up, attempting to get his hands under his feet.

Unable to achieve this action, instead his hands connected with his feet. With little elegance Castiel fell to the floor on his back, grimacing slightly as his head hit the wooden boards.

A chuckle came from the wooden wall, and with narrowed eyes Castiel looked over to where Dean was sitting. The pirate was obviously stifling the majority of his laughter, though smaller ones managed to escape him.

Castiel felt the color returning to his face, and he quickly shook his head and managed to get himself back into a sitting position, facing Dean.

The pirate had managed to tame most of his laughter, calming it down to a small fit of chuckling.

"So sorry I can't do everything perfect like you," Castiel snapped, the back of his mind thinking he would get a rise out of Dean and they would end up arguing like yesterday all over again.

To Castiel's surprise though, Dean raised his eyebrows challengingly and threw on his classic smirk. "Pretty boy thinks I'm perfect at everything, eh?"

The color that had been leaving Castiel's face returned instantly, and the former sailor had never felt so red in the face before.

"No, that's not what I- I was just saying-" Castiel realized that he was stuttering and immediately shut his mouth, blushing madly.

"S'okay, Cas. I get that all the time," Dean winked as his smirk transformed into a dazzling smile.

If Castiel thought he had been blushing before, now he was sure that his face was nothing but dark shades of red. He couldn't handle all of the pirate's remarks, Dean was a whole different kind of beast that he'd never had to deal with before.

"You know Cas, most people could take you blushing like that as a sign; any thoughts you'd like to share?"

"What?" Castiel managed to croak out, cursing silently at how his voice seemed a bit higher pitched as he spoke.

Suddenly Dean broke into another fit of laughter, and Castiel watched as the pirate finally quieted down. A large smile remained on his face as he observed the former sailor's face.

"Man you are seriously red in the face, I'd never take you as someone who'd get so flustered."

"I wasn't flustered," Castiel defended, the color beginning to leave his face.

"Sure," Dean replied, though both his tone and his eyes spoke of a different answer. Castiel watched then as the pirate got to his feet, and he walked over to where the former sailor sat.

"Come on, let me show you how it's done." Dean held onto Castiel's arm, trying to pull the former sailor to his feet.

But both froze as they heard the door to the brig being unlocked.

"Shit," Dean whispered before letting go of Castiel's arm, who then fell back onto the floor.

"What a gentleman," Castiel muttered under his breath, bringing himself up to his feet once more.

He watched as Dean then jumped up, his knees hugging his chest tight while he was in the air, bringing his hands under his feet and behind him. With a thud his feet were back on the ground, and he looked at Castiel with a teasing smile.

"I guess I am pretty perfect, huh?" Dean remarked.

Castiel was about to reply, but the door opened and with it came a pirate wearing a familiar smug look.

Ruby looked to Dean, for a moment her eyes switched to black and the action caused Castiel to suck in a large breath to hold back voicing the words that formed in his head.

"Captain wants to speak to you," Ruby told the pirate, and Castiel glanced at Dean. Dean seemed unphased, though the former sailor caught sight of his jaw clenching slightly.

* * *

Dean didn't react when the pirate, he recalled somehow that her name was Ruby, told him that Meg wanted to see him. Honestly, he had been expecting it.

Of course that didn't mean he was pleased by the idea of another encounter with the demon pirate.

"Does she now? It would've been nice if she let me know earlier; my day's already planned."

Ruby raised an eyebrow, "Oh, really?" the demon pirate asked coolly.

"Just a bit, yeah," Dean replied, his stare confident as he looked back at Ruby.

"Too bad princess," Ruby said as she unlocked the door to the cell, glancing over at Castiel in warning.

Dean looked back at Castiel, and he gave the former sailor a small smile before he walked out of the cell.

He narrowed his eyes at Ruby, but the demon pirate simply took hold of his arm and led him out of the brig. Her grip seemed to be as solid as stone as she pulled him along, leading him down the long corridor.

Climbing up the stairs, Dean blinked as he looked up into the sky. Noticing the sun, Dean assumed that it was probably almost noon.

Trying to get a look at the surroundings, the pirate was disappointed to see that there was a lack of land. Instead Dean cast his eyes around the deck, watching the other demon pirates running around on _his_ ship.

_Balthazar better hurry his ass up_, the pirate thought as Ruby brought him to _his_ quarters. She knocked on the door, and Dean frowned as he heard the familiar southern drawl.

"Come in." Ruby rested her hand on the doorknob and twisted it, swinging the door open. A small pit was beginning to form in Dean's stomach while what remained locked in his steel trap began to scratch at the walls.

Stepping into _his_ office, Dean was a bit pleased to see that most of his stuff remained untouched. What caused him to narrow his eyes was the sight of Meg.

The captain sat comfortably in _his_ chair, her boot-covered feet resting on _his _desk. A smile grew on her face as she saw Dean, her dark eyes twinkling.

Meg nodded to Ruby, who released her grip on Dean's arm before walking out of _his_ quarters, shutting the door behind her. Dean remained rooted to where he stood as Meg walked out from behind the desk. She stopped in front of it, crossing her arms as she leaned against it.

That bothered him a great deal, it wasn't too long ago that Dean himself had sat the exact same way.

"Hey there, Dean." Meg greeted, pulling Dean out of his head.

He kept his eyes narrowed as he replied roughly, "Meg. I see that being a captain hasn't changed you much."

"You'd be surprised. How's the unicorn's head?" Meg asked casually, her gaze raking over Dean's face to watch his reaction.

"He'll be fine," Dean answered, thankful he was able to cover the concern that he felt in his voice.

"You never told me his name."

Dean paused, remembering the power a name holds. Names were how you earned reputations, and the pirate didn't want Castiel to build one with demons of all things.

So Dean improvised, as was his specialty.

"What's it to you?"

Meg grinned, "Good to see you aren't too much of an idiot. But come now, no need to worry. I don't have much use for someone like him, just curious as to what you're unicorn's name is."

"Why do you keep calling him a unicorn, Meg?"

"Name first, questions later Dean-o." Dean clenched his jaw, his eyes looking around the room before he released a sigh.

"His name's Clarence Smith." He watched as Meg's eyebrows raised in surprise and suspicion.

"Clarence?" Meg repeated, doubt obvious in her eyes. Dean shrugged.

"It's not like I'm the one who named him," he defended. The pirate held his breath as Meg contemplated the name, and he gave an inward sigh of relief as she nodded.

"Clarence Smith, how wonderful."

Dean remained wary of Meg as he moved away from the door, making his way slowly around the wall.

"What's the plan here, Meg?" He shifted his gaze away from the large window and back towards the demon pirate.

"Wow, Dean. I'm surprised at how quickly you bounce back. Although it's hard to forget how you were just the other day. I found it quite lovely, going back down memory lane. Glad to know that you haven't really forgotten all the great times we ha-"

"Shut it Meg," Dean growled as he clenched his eyes shut, shaking his head. He could feel her eyes looking at him, staring at him with curiosity.

"Touchy, are we?"

Dean didn't answer as he leaned against the wall, his eyes still shut as he tried to focus. The steel trap in his mind was poking and prodding at him, fighting at the blockage that prevented it from leaking out. He trained his attention onto the crack, reinforcing it. To his relief, the fight from the inside gradually died down, and his shoulders relaxed as he opened his eyes.

"Meg, cut the crap and shed some light."

He watched as the demon pirate pouted mockingly, the bottom of her lip jutting out. "But things were just getting interesting."

"Look," Dean started as he took slow steps, the distance between him and Meg gradually decreasing. "We both know the rules, so we both know why you have not and will not kill me."

"Sadly," Meg replied dryly.

"Now enlighten me, what's your options?" Dean now stood only inches away from the captain, her eyes dangerous while she continued to lean against _his_ desk. At first she just frowned at Dean, but then Meg's face transformed, her eyes bright while she wore a confident smirk.

"We're already reminiscing, so I thought why not get even more nostalgic, right?"

For a second Dean paused, analyzing and dissecting Meg's coded message. Once deciphered, Dean's eyes grew wide as realization dawned on him.

* * *

**DUN DUN DUN! Hope you enjoyed and will be there for the next installment! Please review, favorite, or follow if you enjoyed! A lot more will be revealed with Dean coming up, so be prepared!**


	18. Instincts and Responsibilities

**And We're Back! I'm sorry for the delay guys, but I had to go through bandcamp this whole week from 8-4:30; kind of put a damper on my time to write. Anyways, thanks to fictionfairytalesfantasy4921, lindsay16, Sakari Kateri Azrael, Air Guitar Pixie, DeerTopus C. for reviewing! A thanks as well to those who have followed and favorited, I really appreciate it guys x3 Now on to the story!**

_"Look," Dean started as he took slow steps, the distance between him and Meg gradually decreasing. "We both know the rules, so we both know why you have not and will not kill me."_

_"Sadly," Meg replied dryly._

_"Now enlighten me, what's your options?" Dean now stood only inches away from the captain, her eyes dangerous while she continued to lean against his desk. At first she just frowned at Dean, but then Meg's face transformed, her eyes bright while she wore a confident smirk._

_"We're already reminiscing, so I thought why not get even more nostalgic, right?"_

_For a second Dean paused, analyzing and dissecting Meg's coded message. Once deciphered, Dean's eyes grew wide as realization dawned on him._

* * *

Castiel paced back and forth along the edge of the cell while he waited for Dean's return. He felt bad for the pirate to have to go and talk to the demon, but Castiel couldn't help but be slightly relieved at not having to be in the demon's company again.

A bit of color came across his cheeks as he thought back to the kiss he and Meg had shared. He remembered her lips on his own, him trying to pull away despite her arms that were wrapped around his neck like a noose.

But it wasn't the kiss that bothered Castiel so much as the words that left the serpent's mouth when she had whispered into his ear. Even now he could feel her breath hitting his ear as her eyes were filled with a sense of knowing.

"Isn't it interesting that Dean-o's face is a bit angrier than the normal? Just check out how red in the face he is!"

Of course Castiel had come up with different possibilities as to why Dean's face had been red with anger. It could have been due to encountering Meg again, or the fact that his ship had been stolen by a pirate crew of demons.

But Meg's voice still tauntingly sang in his ears, and just the thought made Castiel's eartips burn.

Looking for a hopeful distraction, Castiel tried to roll his uncomfortable shoulders. He imagined Dean's wide grin, his laughter at the former sailor's failed attempt to jump. Annoyance sparked up inside of him, and determination followed shortly.

As high as he could Castiel jumped up, trying to tuck his knees as close to his chest as humanly possible. Quickly he swung his hands, hoping that he could finally accomplish this goal.

A feeling of achievement washed over the former sailor as he looked down to the sight of his own hands.

He couldn't help but give a small smile. _You're not the only one who can do it Winchester._

Flexing his fingers, Castiel's arms relaxed from changing their position. Looking at the cuffs, he noticed how his wrists were red from their clingy companion, the skin raw from the cuffs tight grip.

Pulled from his victory, Castiel froze at the sound of approaching footsteps. He cursed, hoping for a bit more time with his hands now at a better advantage. Listening as the footsteps sped down the hallway, a sense of urgency bubbled inside of him before he jumped up.

Of course, the former sailor had been so focused on listening to the approaching company that he didn't notice the fact that his legs were not as close to his chest as they should have been.

All at once his hands hit his legs and the former sailor collapsed just as the door opened. Panic filled Castiel at the thought of a demon seeing his hands, so he made one last attempt to try and cover up the failure.

The former sailor threw himself to the corner of the cell, curling himself up to try and hide just where his hands were. He clenched his eyes shut as the two entered the room, his heart racing from the scare.

"Cas?" He heard the familiar voice of Dean call out, but he chose not to reply. He could almost imagine the confusion, the concern on the man's face.

_Concern? Is that logical? _Castiel thought as he remained curled up, _why would he be concerned? _

_ Maybe he enjoys making fun of you; his little caged bird, _a different voice responded dryly. Castiel's heart picked up a couple paces, and he tried to take a deep breath that wasn't too noticeable.

His attention was averted from the voice as he heard the familiar sound of a key opening the cell, and he made out the noise that was caused as Dean's holder shoved him in; followed by a slamming door.

In seconds there was a presence beside him, it was warm and its breath seemed to rustle parts of Castiel's hair slightly.

"Cas, man are you alright?" Castiel was silent, until he heard the sound of the wooden door closing. Cracking an eye open, his first glimpse was of a mesmerizing green iris.

And most surprising of all, there was the concern that Castiel had thought he had miscalculated. He squinted as he took in the pirate's face.

"Why are you concerned?" The former sailor asked, not quite understanding why Dean seemed as if he was afraid.

The pirate scoffed, "Because you're still injured, and it doesn't help when you leave and come back to see that the pretty boy with the concussion is curled up in the corner," his face transformed from one of slight humor to serious worry, "now what happened?"

_Man's got to make sure his bird ain't broken,_ the voice sang quietly in his head. Castiel gritted his teeth and blocked it out, doing his best to ignore him.

Castiel's eartips began to burn as he recalled the fall he took moments ago, he wasn't really being careful about the state of his head.

"I'm fine Dean," Castiel reassured. But the pirate didn't seem to believe him, so Castiel unraveled himself, stretching out his legs to reveal his hands in his lap.

"I managed to maneuver my hands correctly and was able to put them in front of me. Regretfully, this didn't happen until you were already on your way back down; I had difficulty going back to my original position so I improvised."

Dean stared at Castiel in silence for a moment, thinking over the former sailor's answer in his head. Castiel watched curiously, confusion settling in after still noticing the concern chiseled into Dean's features.

"Difficulty going back to your original position?" Dean repeated with a raised eyebrow, and Castiel's eartips continued to burn as he let his embarrassment show.

"It could be possible," he began slowly, "that I may have not been focusing too much on the position of my knees when I jumped due to my attention being more trained onto your approach." His eyes searched Dean's face, watching as the pirate held his raised eyebrow.

Suddenly what had been a face full of worry flushed away as a smile appeared on Dean's face, his eyes twinkling with amusement.

"You fell again," he deciphered as his grin grew larger. Castiel narrowed his eyes slightly, but he did so harmlessly.

"That would be correct."

Dean chuckled, it was light and didn't carry around a tone of darkness whatsoever.

"Man, you had me going there. It's not funny when you screw with people and make them worry Cas," Dean's face grew a bit serious as he spoke, though teasing was evident in his voice.

"Why were you worried so much about me Dean?" Castiel repeated, staring at the pirate who now stood a bit away.

* * *

Dean paused once Castiel had spoken, interrupting his light mood that had distracted him from his previous engagement.

The pirate frowned, turning on his heels so as to face away from Castiel as he pondered the question.

"I already told you, Cas." Dean answered, surprised as he felt his heart pick up its pace ever so slightly. He could imagine the frown that stared at his back as the former sailor replied.

"You gave me a possibility which I find confusing, Dean. I can understand how that possibility could be entirely true, but considering the way you reacted it reminded me of Ga-"

Dean raised an eyebrow as he turned around to face the former sailor who remained where he sat. Castiel's expression seemed to soften, his eyes glowing with what seemed to be torn between a distant past and the realm of the present.

"Gabriel? You two related or something?" Dean inquired, recalling the guard who had been rather comedic during their first encounter.

"He's my older brother," Castiel replied as he turned his head to face the pirate, their eyes instantly locking onto one another.

Immediately Dean knew why Castiel hadn't finished his train of thought previously. As soon as Dean had seen Castiel he had gone into a mode of himself that he hadn't used in years.

"Gabriel practically raised me," Dean kept his eyes on Castiel's as he was pulled out of his thoughts. "He's a very strange man, perhaps like yourself in some aspects."

Dean smiled faintly, nodding slightly in agreement.

"The reason I mention any of this in the first place is because your concern reminded me of him. An older brother, looking out for the ones they claim to be their responsibilities."

Dean winced as he felt a violent shove from inside of his steel trap, he closed his eyes as he tried to hold back the monster inside. It was like a flood warning, and he couldn't have the dam breaking on him now.

_"We're already reminiscing, so I thought why not get even more nostalgic, right?"_

"Damnit," Dean growled as he unsteadily managed to get to the side of the ship, leaning against the familiar dark boards. He pressed against them, forcing himself to anchor himself to one of the few things that kept him in the real world.

It was mental warfare, the way the beast scraped and prodded with sharp claws at its prison, searching for an escape. But Dean held strong, making sure to not give the creature inside an inch.

The worst part was that it hurt like hell. His head throbbed and it only seemed to be getting worse now with Meg's destination in mind.

"Dean?" A rough voice cut through the dark world, causing Dean and both the monster to break away. Gradually the pirate opened his eyes, noticing now the close proximity that was between both him and the now standing former sailor.

Blinking, the room remained silent save for the waves rocking the boat while the two seemed to hold their breath. Dean cleared his throat, his eyes noticing the way Castiel's face was split between curiosity and confusion as they both stared.

"I'm fine, Cas. Just a headache," Dean lied, in the back of his head he could feel a persistent prodding from the beast. Castiel frowned more so than usual, his brow furrowed as he replied.

"What did Meg talk to you about, Dean?" The pirate inhaled a sharp breath, silently hoping that Castiel wouldn't ask about his meeting with Meg.

_You got him into this mess, _he thought to himself regretfully.

"Not much, except for the fact the bitch is wanting to take a stroll down memory lane," Dean snarled out the last part bitterly, the monster inside growling and snarling at him.

"What do you mean? You were making such a big deal about not dying, any solution to that unanswered question?" Castiel's eyes were boring into Dean's own, and the pirate forced himself to calm down, for his heart not to give away the internal panic that Dean felt. He couldn't tell Cas why Meg can't kill him.

"She's got other ideas for our situation; guess she thinks it wouldn't be as fun," Dean supplied, eyes narrowing at the mention of the demon having fun. He could only guess how much she was going to enjoy getting rid of the both of them.

Castiel nodded, Dean could easily see the small seeds of doubt planted in the former sailor's eyes. But Castiel's determination to interrogate seemed to dwindle away, causing Dean to give an inward sigh of relief.

"So what can you tell me, honestly?" Castiel questioned. Despite his jab at Dean's secrets, the pirate was thankful that the former sailor didn't continue to pry.

Before Dean could answer though both were silent as they heard an unusual amount of noise coming from above them.

Dean swore as he stopped leaning on the wall and turned around, walking to a small hole in the wood that sat a few feet behind him. He stood in front of it, turning his head to try and catch a glimpse of what all of the noise was for.

Then his eye caught sight of something that was distant, a simple blur of green and white that was gradually growing closer.

"I'm gonna kill her," Dean muttered before backing away from the hole. Fuming, the pirate paced around the cell. He watched from the corner of his eye as Castiel moved towards the hole, craning his head around to try and spot what Dean had.

"What is that?" Castiel asked as he caught sight of the nearing figure.

"No place good," Dean grimaced, pausing his constant pacing.

Castiel stood up straighter and turned away from the hole so as to face Dean. The two stared at each other in silence, both their minds racing. One of them was filled to the brim with questions, the other's silent save for the occasional scratch from the monster down below.

* * *

"They'll be coming to get us soon," Dean whispered, his eyes now distant. Castiel narrowed his eyes at the pirate, angered by his sudden change of mood.

"Dean," Castiel snapped, and was pleased to see that the almost glassy look in Dean's eyes faded away as the pirate looked at Castiel.

"What are they going to do to us?" The former sailor asked, the familiar feeling of panic slowly rising up inside of him after seeing Dean's reaction.

"It's not what they are going to do to us," Dean replied, "it's what they are going to make us do."

"And what is that?" Castiel asked, and his breath caught in his throat as he began to hear descending footsteps.

"Nothing good."

"Damn it, Dean! Pull yourself together!" Castiel surged forward at the pirate, his hands twisting into Dean's shirt as he pulled him close.

"I did not try to escape this ship for ten days with you always there to stop me; only to have you now freezing up on me when I actually need you! Come on, you're the great Dean Winchester; one of the most infamous pirates the world has ever known! Now whatever happened to you, I don't give a damn right now. All that matters to me is that you keep yourself together. Do that, and just maybe we can get through this, damn it!" Castiel breathed heavily, his face almost touching Dean's as their eyes remained locked onto one another.

He could feel the anger slowly escaping him after shouting at the pirate; whose whole face was a masterpiece of shock after receiving the outburst. Dean remained speechless, and Castiel searched the pirate's face for any sign of change in attitude.

Out of nowhere a familiar smirk appeared on Dean's face, and Castiel felt his shoulders slump in relief.

"Sure pretty boy, I think I can manage that." His voice was soft as Castiel gradually let go of his shirt.

The former sailor wanted to smile. At this point, he wasn't even upset about the nickname anymore.

* * *

**SO MUCH FLUFF. God I feel bad for what I have in store now xP. Anyways, hope you enjoyed and will favorite, follow or review! See you for the next chapter!**


	19. Corrupted Salvation

**This is it guys, it's finally time to take a look into the past. But first, formalities are in order. This story has reached 100 reviews, and that's so amazing! Thank you DeerTopus C. (I hadn't actually heard that song before so I checked it out while writing this chapter, and you were so right. Reminded me very much about how I wrote Dean 0.o), Kather-Swine(Well, let's just say this chapter will be an example for others to follow, I guess. Happy and sad go hand in hand), lindsay16(Do not fear, I was hoping you'll could at least hold out for a couple of days; I hope the wait wasn't too long, or at least long enough for the suspense to set in), Akayuki Novak(It's always a pleasure, being the writer has its perks; especially when dropping subtle hints of not-so-nice things happening later on), and Air Guitar Pixie(Yesh, fluff :3 thank you, it just kind of came out and now I'm really glad it did. And aye, this be a land full of those awful...**_**cliffhangers *shudders*)**_**. Thank you especially to those who are my regular reviewers, those who have been around since Day One. Seeing those names time after time, well I really appreciate it. Also, thank you to those who have followed and favorited, I send my love to you as well :3 Now, I guess it's time to finally approach one of the many elephants on the ship, here you go!**

* * *

_Out of nowhere a familiar smirk appeared on Dean's face, and Castiel felt his shoulders slump in relief._

"_Sure pretty boy, I think I can manage that." His voice was soft as Castiel gradually let go of his shirt._

_The former sailor wanted to smile. At this point, he wasn't even upset about the nickname anymore._

* * *

"Alright, first you should probably get your hands back; they won't give us too much time before they come down here to get us." Dean spoke, his position as a captain evident in his voice when he talked.

Castiel gave a nod, and Dean watched as the former sailor backed away from the pirate. Appreciation coursed through Dean, although it was polluted with the feelings of shame and guilt.

How could he let himself fall into despair when Castiel needed him? How could he let the monster inside of him deal the winning blow when the fight wasn't even over?

_Not again,_ Dean growled to himself, _One time is good enough for this lifetime_.

Drawn out of his thoughts, Dean's attention was brought onto Castiel who now stood with his hands where they had been originally. He picked out the determination that roared in those familiar blue eyes, and it seemed to boost his own.

Straightening his shoulders, Dean took a step towards Cas. The back of Dean's neck burned as he and Castiel both froze, hearing approaching footsteps.

"Look," Dean hissed hurriedly, "Meg's a bitch and what she's got planned is going to suck for the both of us. The bonus is that she'll have to remove the cuffs; don't ask me why. But you try and stay as close to me as possible okay? Do that and we should be-"

Dean's words were cut short though as the door to the brig opened, revealing the familiar smug form of Ruby; her arms crossed while she grinned. Behind her was another woman, her eyes narrowing at the two in the cell.

"Time to go, boys." Ruby sang as she made her way over to the cell and unlocked the door.

Dean forced himself to breath, to calm the panic that was wanting to rise out of him. Yet somehow he kept himself collected, and with narrowed eyes and decisive footsteps Dean made his way out of the cell.

Immediately the woman who was standing in the doorway stepped forward, reaching out and grabbing hold of Dean's arm.

Ignoring his hammering heart, the pirate tried to push against the beast, who in turn shoved at the crack in the steel trap.

Leaking out, small glimpses from behind the wall escaped through the breaks that were forming in the crack.

_Hands bound, a cold hand wrapped around his arm tightly while the own kept on a cold smile as they walked down the corridor._

The demon pirate began to lead him through the hallway, her face like that of a canvas yet to be drawn in.

_ Eyes, watching his every step as he tried to remain confident, his face stone and his stare only looking at what was in front of him._

As they made their way across, it was becoming more evident that all of the crew was most likely gathered on their deck. Footsteps and chatter growing louder and clearer as they continued on silently.

_Silence was instantaneous as he was brought onto the deck. So many faces looked at him, the majority of their expressions the cold joy that was so common among them; but some almost wore a face that expressed a kind of sorrow. _

Dean clenched his jaw as he and the demon made the ascent up the stairs and onto the deck of the ship, he could feel himself beginning to shake; though it was light and barely noticeable.

_A dense forest sat on the formation of land which the ship floated nearby. The forage was thick and wild, the calls of animals and birdsong faintly carried through the breeze. _

Unable to avoid it, Dean turned his head and couldn't help but freeze where he stood with a sharp intake of breath. The shaking grew stronger, his breath hitched in his throat as he couldn't take his eyes away from the familiar formation of sand and forestry.

The demon pirate that had kept a firm grip on his arm gave an exasperated sigh as she yanked the pirate away from his rooted position; causing him to stumble behind her. But Dean could still feel the island's presence, it never leaving the corner of his eye.

Faintly he could make out the sound of footsteps behind him, and Dean twisted his head barely to see that both Ruby and Castiel trailed a few steps in his wake. Quickly he turned his head around, green eyes scanning across the gathered demonic creatures that all stood at the bow.

_A crew of many at the bow, their silence deafening to Dean as he was not used to pirates, especially demon pirates, being so quiet. The air grew cold as he came closer, able to see his own breath._

_Stop it_! Dean screamed at the monster, who shoved harder at the crack. The reinforcements were giving away, tiny holes expanding into much larger empty spaces. Pouring from them were dark, filthy forms of corruption. Polluting Dean's mind, clawing at him and dragging him away from the real world.

He grimaced as he was assaulted with the poisonous darkness, the way it seemed to swirl and coil around him. Sparsely, he could hear the cold laughter coming from inside the steel trap. It was manic and cold, somehow it even sounded pure to Dean's ears.

Being drawn out of his thoughts, Dean brought his attention back to reality as he was stopped by his holder. He tried desperately to calm his shaking hands with tremulous, deep breaths.

The crowd shook as a form moved its way through, making its way to the front. Watching with narrowed eyes, the familiar figure of Meg now stood at the head of her crew. Tightening his fists behind his back, Dean dug his fingernails into the palm of his hand to try and cease his quivering.

"You should appreciate the effort I put into this little send away, Dean. I figured you would enjoy a little bit of nostalgia before we part of ways."

"How thoughtful," Dean replied through gritted teeth, and he felt the grip on his arm tighten.

"Glad you think so," Meg replied with a smile and a slight tilt of her head. She turned to face the gathered demon pirates, some of their eyes switching between the chilling orbs of black and those which were deemed normal.

"As you all might know, this lovely gentleman is Captain Dean Winchester. Lucky for us, he has been so gracious as to donate his ship for our use, along with his presence for a short period of time." Meg looked back and flashed a grin at Dean, in turn the pirate jerked against his holder's grip; although she held strong.

"Sadly," Meg slumped her shoulders in mocking as she turned away from the crowd and took swaying steps towards Dean, "His time with us has come to an end. So we shall part ways with him here; at his final destination."

Meg's face seemed to light up as Dean continued to glare at her, but he tensed as she raised her hand up towards his face.

Instead, she patted his cheek, "It's been fun, all of this reminiscing, Dean."

"Oh it's been great," Dean snarled before pulling against the demon pirate's grip as he leaned close to Meg, "but if you still have my ship when I get back, I'm gonna be pissed."

Meg smirked, "Wouldn't have it any other way, Dean-o." She jutted her chin out at the one who held him. "Go ahead and take him to the edge."

He watched out of the corner of his eye as Meg walked up to where Castiel stood behind him.

"Hey there, Clarence," Meg drawled out as she stopped right in front of him. Dean panicked for a moment after forgetting to mention to Castiel about his fake name; and he could only imagine the former sailor wearing his confused look.

Turning his head, he saw that Castiel did indeed look confused, and his eyes glanced towards Dean. The pirate nodded rapidly several times, hoping that somehow the former sailor would understand. He watched anxiously as Castiel's brow furrowed.

"How do you know my name?" Dean gave an inward sigh of relief as his message seemed to have been understood by Cas.

"Little birdie told me," Meg replied slowly. She stared at Castiel in a moment of thought before walking back to where Dean now stood, the heels of his shoes on the edge of the ship.

"Now, if memory serves me, you were standing right where you are now." She walked back to where Castiel stood, and grabbed hold of a fistful of his coat. Tugging him forward, Meg led the former sailor away from his previous position, "and _he_ would've been around right here." Placing Castiel a few meters to Dean's right; close to the gathered demonic beings.

Dean stared where Castiel stood, although it wasn't Castiel that he saw.

_Standing to his right was a man who stood tallest among all of the specimen on the ship. Brown, shaggy hair that was longer than Dean remembered it being sat on the man's head. His face was blank, save for the look of resolve on his face. As if the man was victorious, somehow. Dean couldn't stop himself from cracking a bit on the inside, thin lines snaking around his portrayal of confidence. He allowed himself to deflate as the two stared each other down; words unable to escape either of them._

Dean's eyes sank to the wooden boards, his hands beginning to quiver. No longer could he block the escaping pollution; and from the darkness in the inside of the box he could see a cruel smile.

_In front of the rest of the demon pirates stood a few of the supreme, the most loved of the crew. One of them was a woman with curly dark hair that surrounded her face, watching with both a curious and malicious gleam in her eyes. _

"It's too bad that he isn't here, I think he would enjoy seeing you like this," Meg nodded towards the pirate who had remained by his side. Barely he felt the removal of the cuffs, but at the moment Dean's connection to reality was fading; he found himself drifting back towards that awful memory.

_The crowd's attention was drawn away from the two though as a man clad in white stepped out of the captain's quarters. He approached slowly, dominance and authority shouting at everyone from the way he made his way down to the gathering. Both Dean and the tall man gave a sharp intake of breath, and for a moment the Winchester glanced at him before his gaze was drawn back towards the sharp dressed man._

_His cold blue eyes drilled into the form of Dean Winchester; but the pirate did not back down from the challenge. His stubbornness brought a small smile to the dominant figure as he stopped in front of Dean. _

"_Hello, Dean," the man with the short blond hair greeted, the bottom of his face decorated in stubble which shared the same color. Tense, Dean kept his whole body stiff and confident as he replied with a smirk._

"_Wow Old Scratch, you dress that nice just for me?"_

"Although last time it was just one person that departed, so it makes sense for _you_ to go." Dean blinked, unclear as to what Meg was implying while she stood next to Castiel; who wore the same expression as the pirate.

"But you see, this one right here could be a keeper," Meg dragged out before looking directly at Dean with a wide grin. "Just imagine all the fun I could have with this one."

Both Dean and Castiel's eyes widened, the former sailor looking to Dean who stood speechless, save for the feelings of anger that overrode all others.

"Meg-" Dean growled, but the demon captain interrupted as her eyes flashed black.

"Hell, give him a couple years and then we would have some real fun, right Clarence?" Meg batted her eyes at the former sailor, whose eyes narrowed at the demon as he continued to wear a look that carried both a frown and panic.

"_Glad to see that even at the end you haven't lost your humor," Lucifer commented as he continued to adorn a small smile. "I will miss that most, I think." The captain rested a hand on Dean's shoulder. Turning to face the crowd, Lucifer's grip on Dean's shoulder tightened, a feeling of cold spreading throughout the pirate's body._

"_As you all know, we are gathered here today to say goodbye to the soon-to-be departed; the charming Dean Winchester. Lord knows we've had to put up with him for awhile," a couple of snickers and cackles escaped the crowd of demons._

"_Now, personally I'm bittersweet," Lucifer turned to face Dean once more, "you were such a pleasure to have around." Dean could feel his stomach churning as he looked into the devil's face, both of them thinking back to their history with one another._

"_But it's okay, because even though today we lose a crew member, one is gained as well." Lucifer raised a hand, gesturing towards the tall man that stood to Dean's right. The tall one was silent, his face blank and unaffected._

_Satan shrugged mockingly, "Guess he's not much of a talker."_

_Lucifer turned his attention back to the younger pirate, whose eyes were locked onto the taller of the two. It was easy for Lucifer to identify the way that Dean was looking at the other, he had been the recipient of such a look many times in his childhood._

_Leaning in close, the devil whispered into Dean's ear._

"_This may pinch," he warned before his hand shifted towards the back of Dean's neck, and he began to chant with a low voice._

"_Te solutum fuerit debitum. Et dimittetis evasit. Tenet noctis mundavero vos ab illo vinculo animus. Et nunc absolvo vos. Ego te absolvo. Rursus in arma proficiscor humanitatis; daemonem."_

"So you just going to stand there, or is someone going to have to push you; _again_?" Dean's heart hammered in his chest as he brought himself back to focus again, eyes locking onto the forms of Meg and Castiel. Meg's entire face was confident, glowing with pride and sarcasm.

Castiel stood near, his whole face illuminated by the sheen of panic and confusion. His eyes were wide with alarm and fear, unable to decide on a course of action. For a moment, the world was silent as they both stared at each other.

And it only took that one moment where the world seemed to stop spinning for Dean to decide.

He.

_The back of Dean's neck burned as he felt the black smoke that had tainted the very core of him release its grip._

Promised.

_All of the corruption it carried was locked away, and within the steel trap sat a monster. A monster that welcomed the feelings of cruelty. A monster that would later on pound at the walls, wanting to taste freedom again, to put its dark skills to use in the real world._

That.

_He felt his balance slip away as he tottered back and forth. With a grin Lucifer released his hold on Dean after pushing him._

"_Bye bye," the devil whispered as he watched the falling form of Dean Winchester._

He.

_Time seemed to slow as Dean's feet left the floor, and suddenly he was a feather caught in the breeze; the lapping of waves cheering as he descended. _

Would.

_The tall figure leaned over the railing, emotions breaking through the stone mask that he had worn for so long after being weathered by such events of despair. Dean felt a piece of his heart break, something that he hadn't felt in ages, as he caught sight of the face._

Keep.

_Eyes that he had only seen through a filter of cold and heartless now seemed to be free, drinking in everything with a new perspective. The sun was shining, a blue sky that was much more tame compared to its darker counterpart._

Himself.

_Locking in on the face, Dean stared at it; drinking in all of the details that he hadn't bothered to notice moments before. He could almost make out the eyes, almost make out of what they were screaming that the tongue refused to share._

Together.

_Before he was enveloped with the waves, Dean felt as if he had finally woken up. And after waking up, despite the damage that had scarred and changed the look in those eyes and that face, a day wouldn't go by that he wouldn't recognize it._

_His back met the brutal ocean as he found his voice, his first word as a freeman escaping from his lips._

"_Sammy!"_

"No, I've got it covered," Dean uttered before he lunged forward, his hand finding a fistful of a surprised Castiel's coat. Meg began to drew her pistol, but Dean was quicker as he threw his foot into her abdomen and the demon captain was launched away from the two.

Immediately the entire crew had their weapons drawn, and bullets were launched at the two.

Dean pulled Castiel behind him, the former sailor lost in a whirl of confusion as he tried to find his footing while trying to avoid getting shot. It only took a bit for them to reach where Dean had stood, and blocking his escape was his holder.

The pirate stopped short as she held her blade out, battle-ready. Quickly, Dean threw Castiel against the railing, the former sailor in a complete state of shock. Dean held him by the front of his coat with two hands.

With both of their eyes wide, Dean couldn't help but give a grin of reassurance to the baffled sailor.

"Don't drown," Dean ordered, and before Castiel could reply the pirate shoved forward. Yelping in surprise, Dean watched as the former sailor fell to the waters below.

Looking back at the others, he saw now that they surrounded him, Meg standing in front of the others. Even with her black eyes Dean could easily tell she was pissed.

"You're lucky that I can't tear out your throat," she hissed. Dean didn't reply, instead his eyes taking in all of the pistols and swords drawn and pointed at him.

Focused, Dean smirked at the angered demon, "Come on Meg, I'm Captain Dean Winchester. Luck's got nothing to do with it," Dean replied before turning and jumping over the rail. His leap of faith was quickly followed by the sounds of multiple pistols firing in his general direction.

He bit back a scream as his right leg was hit by ammunition, his eyes watering before he impacted with the ocean's surface. The water didn't help his leg as he drifted underwater for a moment, wrapped in the arms of a peaceful calm that did not mirror the surface.

Resurfacing, Dean looked around to try and find Castiel. Doing his best to ignore the throbbing pain in his leg, the pirate began swimming immediately towards the familiar form of the former sailor.

"Cas," Dean tried to call out, but he was only met with the water's repetitive noises. He watched with a slight horror as the figure seemed to be still, and Dean desperately swam closer.

Finally reaching Castiel, Dean grabbed the former sailor's face. His eyelids were shut as he stayed on the water's surface, floating. Relief washed over Dean though as he felt the familiar throb of a pulse on the former sailor.

Coming to the conclusion that Castiel must have landed on his head when he fell, Dean cursed as he grabbed hold onto the collar of his coat, "Frickin' concussions man," he muttered in between strokes.

Tugging Castiel along, Dean was exhausted once he managed to reach the shore of the familiar island. Breathing heavily, Dean pulled both himself and Castiel away from the water before he collapsed onto the beach next to the former sailor.

"We're okay, pretty boy." He whispered to the unconscious man before he too drifted off into the comforting, thoughtless void.

* * *

**Wow, this chapter was certainly one of the larger, more complicated chapters that I've written. I hope you guys enjoyed it, now that you got a peek behind the curtain with Dean. Then again, there's still much more to tell about all of them! Please review, follow and favorite if you enjoyed; it means a lot! See you for the next installment!**


	20. Immersed in the Unknown

**And it's time for a new update! I apologize for how long it took, but I won't list talk too much about it up here. SO, thanks to Akayuki Novak(That he is, and as for Sammy…), lindsayd16(Thank you! Dean's backstory is certainly...interesting to say the least), fictionfairytalesfantasy4921( Maybe not quite, although it's nice to hear theories ^_^), DeerTopus C. Von ZenHousen(Thanks for the music suggestions, you definitely have a point), Allison(Sorry that it wasn't soon, but here it is. Thank You!), FandomTiger( Thank you, glad you're enjoying it!), and Air Guitar Pixie(Questionable stains, eh? Sounds lovely. As for Dean, I wouldn't necessarily say he was possessed… And as for Dean and Castiel on the island, let's just say I have plans for that lovely little spot. Besides, it's my duty as a writer to cause some sort of emotional reaction, whether it be happy or sad; although it seems I have been leaning a bit toward the latter xP And that chapter was definitely my favorite one to write so far!)**

* * *

_"Cas," Dean tried to call out, but he was only met with the water's repetitive noises. He watched with a slight horror as the figure seemed to be still, and Dean desperately swam closer._

_Finally reaching Castiel, Dean grabbed the former sailor's face. His eyelids were shut as he stayed on the water's surface, floating. Relief washed over Dean though as he felt the familiar throb of a pulse on the former sailor._

_Coming to the conclusion that Castiel must have landed on his head when he fell, Dean cursed as he grabbed hold onto the collar of his coat, "Frickin' concussions man," he muttered in between strokes._

_Tugging Castiel along, Dean was exhausted once he managed to reach the shore of the familiar island. Breathing heavily, Dean pulled both himself and Castiel away from the water before he collapsed onto the beach next to the former sailor._

_"We're okay, pretty boy." He whispered to the unconscious man before he too drifted off into the comforting, thoughtless void._

* * *

Castiel's breath was slow and peaceful as he tried to get closer to the feeling of warmth that was nearby. His mind felt foggy and thick, yet he found the heat comforting. Little waves of serenity seemed to flow from it, he could hear them lazily washing against the shore.

_Feelings don't make sounds_, he heard something mumble in the back of his head. Dazed and confused, Castiel's eyes fluttered open. With tired eyelids the former sailor found himself staring at a scenery of vibrant, clear blue waves rolling onto white sandy beach.

Admiring the view for only a moment though, because the end to his slumber brought about a harrowing headache. Castiel cringed, although he was being pulled back into reality thanks to his head.

It was then that he felt a slow rising and falling that his head rested on. Castiel's eyes grew wide, bringing him completely out of the comfort of rest as he realized what his head was laying on.

Castiel sprang back, jerking his head up unwisely. His actions were followed by an even greater throbbing headache. He gazed at what his head had been resting on, which was the slow rise and fall of Dean Winchester's chest.

Red began to seep into his face, something Castiel found himself doing more and more in the pirate's presence.

_Natural instinct,_ Castiel reasoned despite his embarrassment, _it's common to seek out a sense of warmth and comfort when you're sleeping, or injured._

Despite the logic though, the former sailor almost felt disappointed at his excuse. Glancing at Dean again, Castiel found his eyes drawn to the pirate's face. The many freckles that were speckled around the Dean's face, how _peaceful_ he looked as he slept.

Castiel frowned as he felt as something strange seemed to bloom in his stomach, and he shook his head to try and clear it away. It was different, a feeling that Castiel couldn't quite identify; which was uncommon for the former sailor.

Drawn out of his alien emotions, Castiel watched as Dean's brow furrowed in his sleep, his mouth forming a thin line. Barely, the former sailor observed as Dean's mouth opened slightly, and began spewing sounds from his mouth.

Scooting closer, Castiel leaned forward, trying to make out any of the gibberish that the pirate was uttering.

But it was just a constant stream of words, until Dean seemed to give the smallest sound that Castiel couldn't decide if he had just imagined the noise.

It sounded like the pirate had _whimpered_.

Castiel held his breath as he listened closely, and only a moment passed before the same, small whimper that he had heard previously was uttered again.

"Dean," Castiel spoke up cautiously, deciding he should try to wake him up. But Dean did not stir, instead his face seemed to contort as if he was in pain.

"Dean," Castiel repeated louder, unable to do anything else as the pirate released another whimper that had been louder than those before it.

"Dean!" The former sailor shouted, hoping that finally Dean would stir, would open up those green eyes and taken away from whatever nightmare that he was experiencing.

But Dean did not stir. There was no sign that he had even been affected by the former sailor's voice. Rather than wake up, Dean's eyes were shut as he continued to wince and whimper.

Castiel growled with determination, trying to find his feet. But as the former sailor made a move to stand, his vision swam with an onslaught of black spots. Unsteadily, Castiel sank back down onto his knees. He had been so focused on Dean that he'd been able to block out the majority of his own problem, but now his enemy had regained strength in its pause and attacked Castiel's conscious.

"Dammit," Castiel muttered before he fell back, barely able to recognize the action as his eyes rolled back and he was swamped by a cover of black that was as empty as oblivion itself.

* * *

_Green eyes that were wide with fear looked straight forward as Dean sprinted. His legs carried him stride after stride as he raced along, searching for an escape. He was surrounded by dark, suffocating walls as he traveled through the hall. His own paintings, his creations, screaming at him as he quickly passed them by._

_ Swirling black smoke chased the pirate, reaching out with dark tendrils to try and envelop him in its toxic grasp._

_ No matter how hard he ran though the poisonous form and its master grew closer and closer. Desperately, Dean dragged his gaze around his environment, and it was then that he caught sight of the door._

_ Fear raced through his veins, cold that almost brought about shivers which chilled him; knowing what was held behind that door._

_ But one glance behind his back and Dean decided his decision. Flinging himself at the door, Dean tried not to read the words that declared the room which waited for him as he entered. _

_Eyes only flicking towards the sign a moment before he pulled the door open, Dean tried to take a deep breath as he read the perfect, black letters that sat neatly on a plaque. _

_Art Studio._

_Despite the small trembling that was spreading across all over Dean, the sight of the name caused Dean to lower his eyelids as he muttered in irritation, "Dick."_

_The pirate turned and closed the door behind him, glimpsing the familiar beast that claimed the box as its domain. _

_A small sigh of relief escaped Dean's lips once he was safely behind the door, though his comfort was only for a moment before he turned to face what was so lovingly titled, "Art Studio"._

_Ivory walls surrounded him, their alabaster color causing Dean to frown. The color itself reminded himself of the man who wore frosted fabric that could never be stained._

_Dean shuddered, forcing away hideous memories that he didn't want to add on to his current burden._

_Sitting in front of him a couple meters was a chair, which chose to place itself in front of a canvas._

_Hesitating, Dean stared at the wooden chair before taking cautious steps towards it._

_Standing in front of it, he couldn't take his eyes off of the chair as the pirate contemplated whether or not to sit down._

_Looking for reassurance, Dean cast his eyes about the room. Yet the only answer he received was pure silence from the walls. Pursing his lips, Dean nodded to himself._

"_What the hell," Dean finally decided before glancing back at the exit, "It's not like I'm going back there anytime soon."_

_Before he could change his mind, Dean slumped down into the chair, tense to see what would happen next. After a few moments had passed and nothing of a serious or dangerous matter came about, Dean relaxed slightly. _

_Curiously, Dean stared at the canvas that waited to be filled in. It gave off an odd presence, yet the pirate couldn't quite place how it settled with him. Beginning to feel uneasy, Dean was about to get up from the chair when suddenly colors began to blossom on the white surface of the canvas._

_Catching his breath, Dean watched as dark shades of green filled the majority of the paper, while brown sprouted about in varying places. Soon Dean began to recognize what was being painted, although he didn't recognize the area specifically._

_A last few details were added before the picture ended, the image of forestry complete. At first Dean simply stared in awe, his eyes taking in the explicit care and detail that the canvas had magically created._

_Gradually Dean lifted his hand up, and slowly reached out to touch the image with trembling fingers. _

_His hand reached the paper._

_Out of nowhere light enveloped the entire room once Dean had made contact with the picture. Screwing his eyes shut, Dean was unable to even release a shout of surprise as he felt like he had been moved._

_Disoriented, Dean tried to calm down before opening his eyes. Confused, he stared around where he now stood._

_Surrounding him were thick, dark brown trunks that held vibrant green leaves high above. Bits of sunlight streamed through the cracks in the canopy, and if not for the sudden change of place, Dean would have thought it beautiful._

_The strangest part to Dean though was the familiarity, he just couldn't quite place it. _

_But then it seemed to change, suddenly the pirate felt as if he was frozen, and he watched as his hand lifted up._

_Yet Dean didn't raise his hand. His body began to move, panic swelling inside of him. _

"_What's going on?!" Dean tried to shout, but his voice failed to work._

_There was a blur as something raced away in the corner of his eye. Dean, or Dean's body, gave chase, sprinting after the mysterious figure. _

_ Unable to control his actions, Dean searched for any sign of help, or at least an explanation. His gaze trailed down to his hand, and it was then that Dean recognized that he was holding onto a weapon._

_ It was a strange object, the blade was a type of stone that was oddly-shaped and looked quite deadly; not to mention strange and intimidating. The handle seemed to be made of bone; Dean tried to convince himself that it was not from his own species._

_ Putting his attention back onto the blur, Dean began to see that it was not a creature, but a human. Picking up the pace, Dean's body surged forward to try and catch up._

_ Deja Vu overwhelmed the pirate, yet his mind seemed to hide the answer from him. His own conscious taunting him, shoving familiarity in his face while he couldn't figure it out. The sense of recognition came hand in hand with a feeling of dread, and this escalated Dean's frustration as he grew barely a foot apart from the running man._

_ Without warning, Dean's body reached out and jumped at the man, his free arm trying to wrap around the stranger's neck as they tumbled into a clearing. _

_ The man managed to unlodge himself away from Dean's grip, and did his best to scurry across the clearing on his hands and knees._

_ But he couldn't escape Dean, or rather his body. Dean himself could feel the cold and calculating thoughts pressing down on him as he got to his feet and walked slowly over to the man._

_ The pleading that the stranger spewed from his mouth fell on deaf ears to Dean's body, but Dean watched through his own eyes as he began to attack the man._

_ After battering the man until he was extremely bloody and bruised, Dean's body dragged the victim over to a tree, throwing him against the trunk. No more fight left in the man, all that escaped him were small whimpers and the repeated prayer of "please please please please…"_

_ "Where is he?" Dean asked, although his conscious was still trying to comprehend what was happening. By now Dean had figured with dread that this was a memory, but it was frustrating as well. Why was this happening? What happened here that was hidden to him?_

_ Of course Dean had always known about the monster in his head, he had assumed that upon entering the room that it would show a different story. _

_ But this was new, or old. This was something that Dean hadn't thought of, because there was no possibility of him ever conceiving that there would be more. The wall protected him, and he had always thought he at least knew the beast in which he restrained._

_ Yet here he was, caught off guard with something new; or old._

_ Drawing himself out of his thoughts, Dean turned his attention onto the man that lay against the tree. His body had crouched down to be more level with the stranger, intimidation and threat spoke from every part of his posture. Gripping the weapon tightly, Dean's body moved his strange blade closer to the man's throat._

_ "Where. Is. He?" Words that Dean had not intended to speak escaped from his mouth, and the stranger seemed to tremble more so than previously._

_ "I don't know, l don't know, I don't know," A cold smile that caused Dean to shudder inwardly was placed on Dean's face. Immediately Dean noticed how his body moved his arm behind him, and what followed was a dagger that became implanted in the man's thigh._

_ "Let's try again," Dean spoke with almost a tone of pleasure as he heard the victim's screams, "Where is he?"_

_ The man whimpered, and Dean sighed before applying pressure down on the blade. Quickly the stranger paled and released a cry of pain._

_ "Last time I saw him going to the main island," the victim finally answered, Dean noticed the way he bit the bottom of his lip to try and hold back more cries of pain._

_ Dean's body nodded, pursing his lips before a thin smile came onto his face once more._

_ "Thank you," the pirate replied, and Dean watched as his arm with the strange stone weapon was brought back. _

_Swiftly and forcefully, Dean gave the stranger the companion of death. Once the blow had been dealt, Dean reclaimed his small dagger from the man's corpse, wiping the blood off on the victim's ragged trousers. _

_Standing back up, the pirate left the clearing, his body seemingly knowing exactly where it was going. It still felt strange, the way Dean could see through his own eyes, yet he felt so disconnected from the rest of himself._

_As he walked through the woods, his feet quietly stalking across the undergrowth, Dean began to try and organize his thoughts._

_Obviously he was,(or had) searching,(or searched) for someone. But once more his brain danced away from his reach, twisting away from his grasp so as to leave him to draw a blank._

_What he noticed at once was how his body(or himself) had enjoyed torturing the stranger. If Dean would have guessed, he would have assumed this was while he was with Lucifer's crew._

_But that doesn't fit, because Dean could recognize those dark feelings that had tormented him, the poisonous memories that plagued him most nights._

_But this felt different, almost pure, despite his lack of knowledge. Obviously it was having an affect on himself, the way it seemed to touch his very soul. Even now, Dean could faintly identify what his body was feeling. It was if it was in a constant state of adrenaline, his whole body alert of his surroundings while almost a desire to find the next victim was flowing inside of him._

'_So if it's not then yet, then what is it?" The pirate asked himself, frustrated as he fought to find an answer._

_At first Dean didn't notice that his body had stopped moving, but then he brought himself out of his own thought process._

_He was now standing in a smaller clearing, one that was a decent amount of distance away from the original clearing._

_Inside the clearing near the center was another man. He was sitting down, a long and navy-blue coat in decent condition resting by his side. Despite the state of his coat, it was opposite the the state of the shirt and trousers that he wore; both were stained with all sorts of marks. _

_In his hands was what looked like a photo, and he stared at it with both love and forlorn evident in his gaze. A million ideas came across Dean's mind as he saw the man still staring at the piece of paper._

_Suddenly the man seemed to realize that Dean had been standing there, and he looked up in surprise and greeting. Briskly the stranger folded the picture and slipped it in between the folds of his nice coat. Rising up, the man attempted to brush off some of the dirt that had collected on his black pants._

_Looking back at Dean, the man smiled amicably before speaking with a strong accented voice._

"_Well brother, how's the hunting?"_

* * *

**Once again I would like to apologize for how long it took to update this! School started for me and this first week has been rather time-consuming!Another reason I had taken so long was because I didn't know how I wanted to write this chapter and part of what it involves for Dean. But rest assured, I had a breakthrough and now I should be able to get the words flowing a lot faster.**

**Anyways, enough with the excuses! I hope you enjoyed and leave a review, follow, or favorite if you did! **

**-Tails**


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